Standard Article

Enantioselective Addition of Organozinc Compounds

Organozinc Compounds (2007)

  1. Kenso Soai1,
  2. Tsuneomi Kawasaki1,
  3. Itaru Sato2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0375

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Soai, K., Kawasaki, T. and Sato, I. 2009. Enantioselective Addition of Organozinc Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Tokyo University of Science, Department of Applied Chemistry, Faculty of Science, Shinjuku-ku, Tokyo, Japan

  2. 2

    Kwansei Gakuin University, Department of Chemistry, School of Science and Technology, Sanda, Hyogo, Japan

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

  • 1
    Introduction
  • 2
    The Mechanism of Catalysis for Diorganozinc Addition to Carbonyl Compounds
  • 3
    Enantioselective Addition of Organozincs to Carbonyl Compounds
  • 4
    Enantioselective Addition of Diorganozincs to Imine Derivatives
  • 5
    Asymmetric Amplification
  • 6
    Asymmetric Autocatalysis in the Asymmetric Addition of Dialkylzincs to Aldehydes
  • 7
    Conclusion
  • 8
    Acknowledgment

Keywords:

  • chirality - role in chemical, biological and material sciences;
  • dialkyl function of dialkylzincs;
  • carbon-nitrogen double bond;
  • asymmetric amplification;
  • asymmetric autocatalysis with high enantioselectivity;
  • chiral compounds as chiral initiators;
  • asymmetric amplification

Featured Compounds

VIEW

  1. 1 - 92
Compound 1
Molecular Weight:263.4183
Molecular Formula:C17H29NO
InChIKey:BRRGNOFUBFINSX-NVXWUHKLSA-N
View compound in article | Full details | Search for this compound
Compound 2
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:XIJAGFLYYNXCAB-KRWDZBQOSA-N
View compound in article | Full details | Search for this compound
Compound 3
Molecular Weight:183.2905
Molecular Formula:C11H21NO
InChIKey:IZSOMXMZBFPQMH-RGOKHQFPSA-N
View compound in article | Full details | Search for this compound
Compound 4
Molecular Weight:185.3064
Molecular Formula:C11H23NO
InChIKey:OOTYBPZITJJUIF-JTQLQIEISA-N
View compound in article | Full details | Search for this compound
Compound 5
Molecular Weight:467.6002
Molecular Formula:C34H29NO
InChIKey:KEYBUYUVPJKTFF-GYXLRUHFSA-N
View compound in article | Full details | Search for this compound
Compound 6
Molecular Weight:232.2783
Molecular Formula:C13H16N2O2
InChIKey:CFEDMIOYNRAPIM-JLLWLGSASA-N
View compound in article | Full details | Search for this compound
Compound 7
Molecular Weight:353.4562
Molecular Formula:C25H23NO
InChIKey:SHLPNNKUDGFFJF-VWLOTQADSA-N
View compound in article | Full details | Search for this compound
Compound 8
Molecular Weight:369.4987
Molecular Formula:C26H27NO
InChIKey:SJAPKZSNWWIRHP-GICFLYKWSA-N
View compound in article | Full details | Search for this compound
Compound 9
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:UOYFLCUGMKLDIV-RNJXMRFFSA-N
View compound in article | Full details | Search for this compound
Compound 10
Molecular Weight:184.178
Molecular Formula:C10H24Li2N2
InChIKey:GBKZJCWYNAQPMX-IFUMRAAOSA-N
View compound in article | Full details | Search for this compound
Compound 11
Molecular Weight:328.4485
Molecular Formula:C20H28N2O2
InChIKey:CAOIUNFSPMSYIQ-ROUUACIJSA-N
View compound in article | Full details | Search for this compound
Compound 12
Molecular Weight:394.4635
Molecular Formula:C23H26N2O4
InChIKey:FZAJIHNUROSLMS-MUGJNUQGSA-N
View compound in article | Full details | Search for this compound
Compound 13
Molecular Weight:794.287
Molecular Formula:C50H40N4O2Zn
InChIKey:NERXQPVVGHBDMQ-HYSICOPKSA-L
View compound in article | Full details | Search for this compound
Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 17
Molecular Weight:388.633
Molecular Formula:C22H32N2S2
InChIKey:IGCRIAODLXTXFQ-VVIORFSUSA-N
View compound in article | Full details | Search for this compound
Compound 18
Molecular Weight:321.521
Molecular Formula:C19H31NOS
InChIKey:OIVMTYAKXHPDCT-VQIMIIECSA-N
View compound in article | Full details | Search for this compound
Compound 20
Molecular Weight:626.55
Molecular Formula:C28H40N2O4Se2
InChIKey:GBQQYFRIAIISQZ-PSWAGMNNSA-N
View compound in article | Full details | Search for this compound
Compound 19
Molecular Weight:270.389
Molecular Formula:C17H18OS
InChIKey:QLYGFHRLLZYYOR-MRXNPFEDSA-N
View compound in article | Full details | Search for this compound
Compound 21
Molecular Weight:485.439
Molecular Formula:C29H35FeNO2
InChIKey:RIGNYGYGOLNVCZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 22
Molecular Weight:461.419
Molecular Formula:C21H27FeNO3S2
InChIKey:LLIJHLGMQFGBPT-VYHHWTHSSA-N
View compound in article | Full details | Search for this compound
Compound 23
Molecular Weight:378.312
Molecular Formula:C8H12F6N2O4S2
InChIKey:GKSGSDYYIYURPD-PHDIDXHHSA-N
View compound in article | Full details | Search for this compound
Compound 24
Molecular Weight:466.5675
Molecular Formula:C31H30O4
InChIKey:OWVIRVJQDVCGQX-VSGBNLITSA-N
View compound in article | Full details | Search for this compound
Compound 25
Molecular Weight:266.3343
Molecular Formula:C18H18O2
InChIKey:BRNWPPMSCLARQU-XSLAGTTESA-N
View compound in article | Full details | Search for this compound
Compound 26
Molecular Weight:947.2062
Molecular Formula:C67H62O5
InChIKey:BZGHBVCOQAYQTL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 27
Molecular Weight:303.357
Molecular Formula:C13H22NO3PS
InChIKey:GDSXLQQRCQNZIB-DGCLKSJQSA-N
View compound in article | Full details | Search for this compound
Compound 28
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:FWVNWTNCNWRCOU-BYPYZUCNSA-N
View compound in article | Full details | Search for this compound
Compound 29
Molecular Weight:543.346
Molecular Formula:C14H25F6N2O6S2Ti
InChIKey:FTBBUDADNMNPSR-SKSSAGQDSA-N
View compound in article | Full details | Search for this compound
Compound 30
Molecular Weight:240.297
Molecular Formula:C16H16O2
InChIKey:XHFVGFDZLPVRCP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 31
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H12O3
InChIKey:YESYELHMPYCIAQ-LURJTMIESA-N
View compound in article | Full details | Search for this compound
Compound 32
Molecular Weight:Not Available
Molecular Formula:(CH2)nC5H8O2
InChIKey:JBFHTYHTHYHCDJ-YFKPBYRVSA-N
View compound in article | Full details | Search for this compound
Compound 33
Molecular Weight:361.498
Molecular Formula:C20H25NO3S
InChIKey:LABUMGDPIXFQON-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 34
Molecular Weight:546.783
Molecular Formula:C26H46N2O6S2
InChIKey:KVVHJCZXSZVOLS-BASDDVJQSA-N
View compound in article | Full details | Search for this compound
Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 36
Molecular Weight:359.4608
Molecular Formula:C24H25NO2
InChIKey:QYSMEBGSHQLGQL-DHIUTWEWSA-N
View compound in article | Full details | Search for this compound
Compound 37
Molecular Weight:254.4115
Molecular Formula:C15H30N2O
InChIKey:VVDSNQLBFFTAIA-RYSNWHEDSA-N
View compound in article | Full details | Search for this compound
Compound 38
Molecular Weight:181.298
Molecular Formula:C10H15NS
InChIKey:VJMIMNPPYKERKN-MRVPVSSYSA-N
View compound in article | Full details | Search for this compound
Compound 39
Molecular Weight:305.392
Molecular Formula:C16H19NO3S
InChIKey:CRZOLKWUJOHXED-BBRMVZONSA-N
View compound in article | Full details | Search for this compound
Compound 40
Molecular Weight:361.498
Molecular Formula:C20H27NO3S
InChIKey:KJXHPMLOYKNALT-IBGZPJMESA-N
View compound in article | Full details | Search for this compound
Compound 41
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:FMCGSUUBYTWNDP-MWLCHTKSSA-N
View compound in article | Full details | Search for this compound
Compound 42
Molecular Weight:482.458
Molecular Formula:C30H36FeNO
InChIKey:PEYYLWOKFBAJCE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 44
Molecular Weight:839.1514
Molecular Formula:C56H70O6
InChIKey:RNXUBQSHYYETNK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 45
Molecular Weight:493.418
Molecular Formula:C30H31FeNO2
InChIKey:MNULATXHUFNUMA-GJICFQLNSA-N
View compound in article | Full details | Search for this compound
Compound 46
Molecular Weight:642.717
Molecular Formula:C28H26NO5Re
InChIKey:WLOZPBXOAPXZFC-VTTXPQSASA-N
View compound in article | Full details | Search for this compound
Compound 48
Molecular Weight:227.323
Molecular Formula:C11H17NO2S
InChIKey:QXEVXIJPLGXBPX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 49
Molecular Weight:539.6027
Molecular Formula:C36H30NO2P
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 50
Molecular Weight:677.8543
Molecular Formula:C42H52N3O3P
InChIKey:DWEURVVUYIGHFA-XGHPZHRWSA-N
View compound in article | Full details | Search for this compound
Compound 51
Molecular Weight:505.453
Molecular Formula:C29H40FeNOP
InChIKey:MLAGJMJODGHTQZ-HMWSMTLBSA-N
View compound in article | Full details | Search for this compound
Compound 52
Molecular Weight:607.7
Molecular Formula:C39H30NO2PS
InChIKey:MRRYJQLJAGHENQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 53
Molecular Weight:914.8718
Molecular Formula:C60H36O6P2
InChIKey:UFQYDYMALACWGX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 54
Molecular Weight:243.836
Molecular Formula:C10H14CuNS
InChIKey:ZHOUMFYVBMMVMO-DDWIOCJRSA-M
View compound in article | Full details | Search for this compound
Compound 55
Molecular Weight:221.2955
Molecular Formula:C13H19NO2
InChIKey:CKYZZANMHFBGRW-DGCLKSJQSA-N
View compound in article | Full details | Search for this compound
Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 57
Molecular Weight:293.4027
Molecular Formula:C20H23NO
InChIKey:MLWAVAXKKWLTEY-YSFGRKDWSA-N
View compound in article | Full details | Search for this compound
Compound 58
Molecular Weight:317.4241
Molecular Formula:C22H23NO
InChIKey:XKGVODLIURNSDV-FCHUYYIVSA-N
View compound in article | Full details | Search for this compound
Compound 59
Molecular Weight:293.4027
Molecular Formula:C20H23NO
InChIKey:JAHYOUBCPZBGCW-OAHLLOKOSA-N
View compound in article | Full details | Search for this compound
Compound 60
Molecular Weight:164.2243
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 61
Molecular Weight:272.312
Molecular Formula:C15H25LiN2O2
InChIKey:DXQKUVFXSQBWSH-UGCKCVLNSA-N
View compound in article | Full details | Search for this compound
Compound 62
Molecular Weight:430.91
Molecular Formula:C12H21BrMgO6Zn
InChIKey:BQCCZMGSDQHTQC-PCZIFVQPSA-M
View compound in article | Full details | Search for this compound
Compound 63
Molecular Weight:477.6365
Molecular Formula:C33H35NO2
InChIKey:KGEHSERUOCIUPB-AJQTZOPKSA-N
View compound in article | Full details | Search for this compound
Compound 64
Molecular Weight:533.6827
Molecular Formula:C36H40NOP
InChIKey:NOQQOIKBFDMSEY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 65
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 47
Molecular Weight:227.323
Molecular Formula:C11H17NO2S
InChIKey:QXEVXIJPLGXBPX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 66
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:WFBCDNSZBBNNON-HNNXBMFYSA-N
View compound in article | Full details | Search for this compound
Compound 67
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:HPAJPZJQZPMVHL-JTQLQIEISA-N
View compound in article | Full details | Search for this compound
Compound 68
Molecular Weight:365.5515
Molecular Formula:C25H35NO
InChIKey:GWQIAQYPISGHPE-DEOSSOPVSA-N
View compound in article | Full details | Search for this compound
Compound 69
Molecular Weight:315.4082
Molecular Formula:C22H21NO
InChIKey:JHXKXSNAJSHMIM-BBQAJUCSSA-N
View compound in article | Full details | Search for this compound
Compound 70
Molecular Weight:195.324
Molecular Formula:C11H17NS
InChIKey:JLIPHJUKNDFHDQ-MWLCHTKSSA-N
View compound in article | Full details | Search for this compound
Compound 71
Molecular Weight:425.989
Molecular Formula:C20H28N2S2Zn
InChIKey:FQDJZQHURZXNSM-GGTCEIRZSA-L
View compound in article | Full details | Search for this compound
Compound 72
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:XDTOFRYDFSACBW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 73
Molecular Weight:364.3774
Molecular Formula:C21H21N2O2P
InChIKey:UPFFCGLFOMACAQ-MDYZWHIJSA-N
View compound in article | Full details | Search for this compound
Compound 76
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:MURQWXKMHQTOOL-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound 74
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 77
Molecular Weight:278.3898
Molecular Formula:C16H26N2O2
InChIKey:XKOSGRLLCWYUOY-HNNXBMFYSA-N
View compound in article | Full details | Search for this compound
Compound 75
Molecular Weight:234.2942
Molecular Formula:C13H18N2O2
InChIKey:FXWUCWNUDMUATM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 78
Molecular Weight:258.137
Molecular Formula:C14H18FeO
InChIKey:JVZLEPWQKGKGDB-WWPIYYJJSA-N
View compound in article | Full details | Search for this compound
Compound 79
Molecular Weight:286.3655
Molecular Formula:C18H22O3
InChIKey:AXJSIUJPNSIDBM-IYBDPMFKSA-N
View compound in article | Full details | Search for this compound
Compound 80
Molecular Weight:152.1937
Molecular Formula:C8H12N2O
InChIKey:VPPNKTHBLIUONT-QMMMGPOBSA-N
View compound in article | Full details | Search for this compound
Compound S-81
Molecular Weight:166.2203
Molecular Formula:C9H14N2O
InChIKey:KDDKUGKMCOOGIH-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound S-82
Molecular Weight:232.3214
Molecular Formula:C14H20N2O
InChIKey:YTRPJBUCFQLYHU-ZDUSSCGKSA-N
View compound in article | Full details | Search for this compound
Compound 83
Molecular Weight:234.3373
Molecular Formula:C14H22N2O
InChIKey:HWWYGHQYFAOULH-YBJDMEARSA-N
View compound in article | Full details | Search for this compound
Compound 84
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:HFDNMBXGAKFEQS-ZDUSSCGKSA-N
View compound in article | Full details | Search for this compound
Compound 85
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:SPBYXNSDWVIIJS-AWEZNQCLSA-N
View compound in article | Full details | Search for this compound
Compound 86
Molecular Weight:277.3603
Molecular Formula:C19H19NO
InChIKey:OLHLKGHEFXHNHZ-IBGZPJMESA-N
View compound in article | Full details | Search for this compound
Compound 88
Molecular Weight:108.0981
Molecular Formula:C5H4N2O
InChIKey:FREJAOSUHFGDBW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 87
Molecular Weight:188.2258
Molecular Formula:C11H12N2O
InChIKey:LFNCODRCVBGYJX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 82
Molecular Weight:232.3214
Molecular Formula:C14H20N2O
InChIKey:YTRPJBUCFQLYHU-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 89
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:IJBONYUNKRDIFC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound R-81
Molecular Weight:166.2203
Molecular Formula:C9H14N2O
InChIKey:KDDKUGKMCOOGIH-SECBINFHSA-N
View compound in article | Full details | Search for this compound
Compound R-82
Molecular Weight:232.3214
Molecular Formula:C14H20N2O
InChIKey:YTRPJBUCFQLYHU-CYBMUJFWSA-N
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 92