Standard Article

Addition of Organolithium Reagents to Double Bonds

Organolithium Compounds (2004)

  1. Hiroshi Yamataka1,
  2. K. Yamada2,
  3. K. Tomioka2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0310

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Yamataka, H., Yamada, K. and Tomioka, K. 2009. Addition of Organolithium Reagents to Double Bonds. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Osaka University, Institute of Scientific and Industrial Research, Osaka, Ibaraki, Japan

  2. 2

    Kyoto University, Graduate School of Pharmaceutical Sciences, Yoshida, Kyoto, Japan

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    RLi Aggregation and Kinetics
  • 3
    Li Enolate Aggregation and Kinetics
  • 4
    Mechanism and Reaction Pathways
  • 5
    Product Selectivity—Addition vs. Reduction
  • 6
    Theoretical Calculations
  • 7
    Diastereoface Discriminating Addition to Acceptors Having a Chiral Auxiliary
  • 8
    Reactions Mediated by an External Chiral Ligand
  • 9
    Application to Asymmetric Syntheses of Biologically Active Compounds
  • 10
    Conclusion

Keywords:

  • organolithium reagents in synthetic organic chemistry;
  • RLi aggregation and kinetics;
  • organolithium reagent addition to double bonds;
  • Li enolate aggregation and kinetics;
  • ET vs. polar addition pathway;
  • product selectivity—addition vs. reduction;
  • radical probe experiment;
  • external chiral ligand-controlled asymmetric conjugate addition technology

Featured Compounds

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  1. 1 - 51
Compound 1
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:MLORIZUOQJTZID-AATRIKPKSA-N
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Compound 2
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:XGBIOFQJXMZZAG-BQYQJAHWSA-N
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Compound 3a
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:PJRHFTYXYCVOSJ-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:ZWSGUNBFJXYDNQ-SNVBAGLBSA-N
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Compound 4a
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:XKGLSKVNOSHTAD-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:KZUUAMNANGAYEP-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:238.3242
Molecular Formula:C17H18O
InChIKey:KRUIOJKRONYXTA-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:222.2818
Molecular Formula:C16H14O
InChIKey:ZLYYQUZSKSMWAG-CABCVRRESA-N
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Compound 5
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:HPEBGANKLUUCRO-UHFFFAOYSA-N
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Compound 6
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:URROMGONCQNNMD-CSKARUKUSA-N
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Compound E-7
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:JRTSXIAOCFBBPE-BQYQJAHWSA-N
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Compound Z-7
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:JRTSXIAOCFBBPE-FPLPWBNLSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:TWLMAJWLUBGUKS-FPLPWBNLSA-N
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Compound E-8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Z-8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:318.4985
Molecular Formula:C16H38N4O2
InChIKey:TZUXVTNMUKCLJY-HOTGVXAUSA-N
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Compound 20
Molecular Weight:87.0773
Molecular Formula:C3H5NO2
InChIKey:RIHXMHKNTLBIPJ-NSCUHMNNSA-N
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Compound 23
Molecular Weight:145.1995
Molecular Formula:C7H15NO2
InChIKey:QNFKYSCVFQTEGB-SSDOTTSWSA-N
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Compound 22
Molecular Weight:204.3098
Molecular Formula:C10H24N2O2
InChIKey:VYQCQNCBTMHEFI-UWVGGRQHSA-N
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Compound 26
Molecular Weight:285.3807
Molecular Formula:C18H23NO2
InChIKey:ZLVGZJFMSSLOTM-INIZCTEOSA-N
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Compound 24
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:GNDHNYOKGXAMOS-AATRIKPKSA-N
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Compound 25
Molecular Weight:202.265
Molecular Formula:C10H11LiS2
InChIKey:GOXJKCHXKMYZIF-UHFFFAOYSA-N
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Compound 27
Molecular Weight:338.528
Molecular Formula:C18H26O2S2
InChIKey:SSEFVIMJHBOBAZ-INIZCTEOSA-N
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Compound 28
Molecular Weight:242.3129
Molecular Formula:C16H18O2
InChIKey:AWRUKIQHUKYALU-HZPDHXFCSA-N
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Compound 29
Molecular Weight:234.3803
Molecular Formula:C15H26N2
InChIKey:SLRCCWJSBJZJBV-ZQDZILKHSA-N
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Compound 30
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:IHTVVXNYOKDJES-ZHACJKMWSA-N
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Compound 31
Molecular Weight:400.5079
Molecular Formula:C24H32O5
InChIKey:KECASTXGCVKDPE-NRFANRHFSA-N
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Compound 32
Molecular Weight:313.3908
Molecular Formula:C19H23NO3
InChIKey:PXLBBXGCEBFGAQ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:339.4281
Molecular Formula:C21H25NO3
InChIKey:HTWZXVVYUAOVOS-DHZHZOJOSA-N
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Compound 34
Molecular Weight:553.704
Molecular Formula:C34H48LiN3O3
InChIKey:KWOIRIGTBXIEHK-SZXYASELSA-N
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Compound 35
Molecular Weight:594.776
Molecular Formula:C37H53LiN3O3
InChIKey:WXKWNDKWYULCDH-FRVOPNQRSA-N
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Compound 39
Molecular Weight:303.783
Molecular Formula:C17H18ClNO2
InChIKey:IJYUPBNUPIRQEP-SATBOSKTSA-N
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Compound 36
Molecular Weight:452.5824
Molecular Formula:C28H36O5
InChIKey:NFXRCRITFDKGCF-UHFFFAOYSA-N
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Compound 37
Molecular Weight:530.6943
Molecular Formula:C34H42O5
InChIKey:UMSQGVMHQUQORU-NGQVCNFZSA-N
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Compound 38
Molecular Weight:283.3648
Molecular Formula:C18H21NO2
InChIKey:NVONXANDMFUUKH-CRAIPNDOSA-N
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Compound 44
Molecular Weight:329.3654
Molecular Formula:C19H20FNO3
InChIKey:AHOUBRCZNHFOSL-YOEHRIQHSA-N
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Compound 40
Molecular Weight:357.4186
Molecular Formula:C21H24FNO3
InChIKey:TWNHULBZDXWUAN-AATRIKPKSA-N
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Compound 41
Molecular Weight:259.4173
Molecular Formula:C12H25NO3Si
InChIKey:VGSPPTJFJGUQQR-BQYQJAHWSA-N
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Compound 42
Molecular Weight:616.8359
Molecular Formula:C33H49FN2O6Si
InChIKey:WBYWGJPOEIBJOZ-KDHKARCHSA-N
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Compound 43
Molecular Weight:561.822
Molecular Formula:C27H48FNO6SSi
InChIKey:SRKSXQBBTQWOOK-ZCYQVOJMSA-N
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  1. 1 - 51