Standard Article

Ferrocene, 1,1′-bis[(2R,4R)-2,4-diethyl-1-phosphetanyl]-, stereoisomer & Ferrocene, 1,1′-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, stereoisomer

  1. Masaki Tsukamoto,
  2. Masato Kitamura

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01622

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Tsukamoto, M. and Kitamura, M. 2013. Ferrocene, 1,1′-bis[(2R,4R)-2,4-diethyl-1-phosphetanyl]-, stereoisomer & Ferrocene, 1,1′-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, stereoisomer. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Nagoya University, Japan

Publication History

  1. Published Online: 16 SEP 2013

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Abstract

original image

Ferrocene, 1,1′-bis[(2R,4R)-2,4-diethyl-1-phosphetanyl]-, stereoisomer

[268220-91-3] C24H36FeP2 (MW 442.34)

InChI = 1S/2C12H18P.Fe/c2*1-3-10-9-11(4-2)13(10)12-7-5-6-8-12;/h2*5-8,10-11H,3-4,9H2,1-2H3;/t2*10-,11-;/m11./s1

InChIKey = CASVFTKJBSCSOD-PHIZCRGKSA-N

original image

Ferrocene, 1,1′-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, stereoisomer

[290347-66-9] C24H36FeP2(MW 442.34)

InChI = 1S/2C12H18P.Fe/c2*1-3-10-9-11(4-2)13(10)12-7-5-6-8-12;/h2*5-8,10-11H,3-4,9H2,1-2H3;/t2*10-,11-;/m00./s1

InChIKey = CASVFTKJBSCSOD-XTQNZXNBSA-N

(ferrocene-based chiral bisphosphetane ligand for transition metals; its Rh complex shows especially high enantioselectivity and reactivity in hydrogenation of functionalized olefins including itaconic acid derivatives2 and β-substituted (E)-β-(acylamino)acrylates 3)

Alternate Name: Et-FerroTANE.

Physical Data: mp 76 °C; [α]D −660°(c 1, heptane) for (S,S)-Et-FerroTANE.4

Solubility: soluble in dichloromethane, chloroform, pentane, and heptane.

Form Supplied in: yellow-orange powder; commercially available.

Analysis of Reagent Purity: the purity of Et-FerroTANE is analyzed by 31P NMR (CDCl3, 162 MHz) δ 13.10.5

Handling, Storage, and Precautions: solid Et-FerroTANE is air sensitive, thus for long-term storage bottles of Et-FerroTANE should be flushed with N2 or Ar and kept airtight.

Preparative Method: enantiomerically pure Et-FerroTANE is obtained by reaction between 1,1′-bis(phosphino)ferrocene and the chiral cyclic sulfate derived from (3S,5S)-heptane-3,5-diol or its enantiomer in the presence of a strong base such as sec-butyl lithium.2, 5

Featured Compounds

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Compound Information
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:ZWWQRMFIZFPUAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:NFOQJNGQQXICBY-RXMQYKEDSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:NFOQJNGQQXICBY-YFKPBYRVSA-N
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Compound Information
Molecular Weight:740.226
Molecular Formula:C32H48BF4FeP2Rh
InChIKey:CNVIALWRHAVOPH-TXIBLIASSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:380.4767
Molecular Formula:C24H28O4
InChIKey:GFNVHWAQRAEXDB-UDWIEESQSA-N
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Compound Information
Molecular Weight:382.4926
Molecular Formula:C24H30O4
InChIKey:NDNCBTZDCNZNFE-HXUWFJFHSA-N
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Compound Information
Molecular Weight:382.4926
Molecular Formula:C24H30O4
InChIKey:NDNCBTZDCNZNFE-FQEVSTJZSA-N
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Compound Information
Molecular Weight:275.2998
Molecular Formula:C15H17NO4
InChIKey:YXLWOASJILPHLE-RAXLEYEMSA-N
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Compound Information
Molecular Weight:277.3157
Molecular Formula:C15H19NO4
InChIKey:OWRXCPCLQZZRJO-CYBMUJFWSA-N
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Compound Information
Molecular Weight:277.3157
Molecular Formula:C15H19NO4
InChIKey:OWRXCPCLQZZRJO-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:219.2365
Molecular Formula:C12H13NO3
InChIKey:MHZDCUVUBSLVDC-FLIBITNWSA-N
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Compound Information
Molecular Weight:221.2524
Molecular Formula:C12H15NO3
InChIKey:KAZREVDICMUGDL-NSHDSACASA-N
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Compound Information
Molecular Weight:221.2524
Molecular Formula:C12H15NO3
InChIKey:KAZREVDICMUGDL-LLVKDONJSA-N
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Compound Information
Molecular Weight:696.129
Molecular Formula:C26H44BF4FeO2P2Rh
InChIKey:WEAWATQFRCCTLY-SVOONZICSA-N
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Compound Information
Molecular Weight:233.2631
Molecular Formula:C13H15NO3
InChIKey:WJRSFHQJGCQSLW-XYOKQWHBSA-N
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Compound Information
Molecular Weight:235.279
Molecular Formula:C13H17NO3
InChIKey:OMSCEOCGWYFCPQ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:235.279
Molecular Formula:C13H17NO3
InChIKey:OMSCEOCGWYFCPQ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:JCJBOLUIGLYOFD-UKTHLTGXSA-N
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Compound Information
Molecular Weight:249.3056
Molecular Formula:C14H19NO3
InChIKey:VHZVNRGPDJDZNN-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:249.3056
Molecular Formula:C14H19NO3
InChIKey:VHZVNRGPDJDZNN-CYBMUJFWSA-N
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Compound Information
Molecular Weight:249.2625
Molecular Formula:C13H15NO4
InChIKey:HHQJJJVOOUPHEH-WQLSENKSSA-N
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Compound Information
Molecular Weight:251.2784
Molecular Formula:C13H17NO4
InChIKey:HPOHGSFWIOTIFP-LBPRGKRZSA-N
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Compound Information
Molecular Weight:251.2784
Molecular Formula:C13H17NO4
InChIKey:HPOHGSFWIOTIFP-GFCCVEGCSA-N
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Compound Information
Molecular Weight:253.682
Molecular Formula:C12H12ClNO3
InChIKey:YVQZNYDNPDUUJY-XFFZJAGNSA-N
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Compound Information
Molecular Weight:255.697
Molecular Formula:C12H14ClNO3
InChIKey:NRUURHSPHDCNCD-NSHDSACASA-N
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Compound Information
Molecular Weight:255.697
Molecular Formula:C12H14ClNO3
InChIKey:NRUURHSPHDCNCD-LLVKDONJSA-N
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Compound Information
Molecular Weight:237.227
Molecular Formula:C12H12FNO3
InChIKey:IFTHWBUFALUECK-XFFZJAGNSA-N
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Compound Information
Molecular Weight:239.2429
Molecular Formula:C12H14FNO3
InChIKey:NJGPMIHLOFWBAL-NSHDSACASA-N
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Compound Information
Molecular Weight:239.2429
Molecular Formula:C12H14FNO3
InChIKey:NJGPMIHLOFWBAL-LLVKDONJSA-N
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Compound Information
Molecular Weight:251.2536
Molecular Formula:C13H14FNO3
InChIKey:CDLULRSTUVOWEB-XYOKQWHBSA-N
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Compound Information
Molecular Weight:253.2694
Molecular Formula:C13H16FNO3
InChIKey:CELLRWLJKLRCRQ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:253.2694
Molecular Formula:C13H16FNO3
InChIKey:CELLRWLJKLRCRQ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:249.2625
Molecular Formula:C13H15NO4
InChIKey:HSRSTTPKFGFLLF-FLIBITNWSA-N
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Compound Information
Molecular Weight:251.2784
Molecular Formula:C13H17NO4
InChIKey:MWXZWZWQNPAZDI-NSHDSACASA-N
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Compound Information
Molecular Weight:251.2784
Molecular Formula:C13H17NO4
InChIKey:MWXZWZWQNPAZDI-LLVKDONJSA-N
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Compound Information
Molecular Weight:278.2607
Molecular Formula:C13H14N2O5
InChIKey:WOIMCMDHPRWVBF-XYOKQWHBSA-N
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Compound Information
Molecular Weight:280.2765
Molecular Formula:C13H16N2O5
InChIKey:WQPSHYWDZWDPBZ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:280.2765
Molecular Formula:C13H16N2O5
InChIKey:WQPSHYWDZWDPBZ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:305.3258
Molecular Formula:C16H19NO5
InChIKey:PDNQTSIFHHZKQF-NVNXTCNLSA-N
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Compound Information
Molecular Weight:307.3416
Molecular Formula:C16H21NO5
InChIKey:IUQVQBCPGJMDKT-HNNXBMFYSA-N
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Compound Information
Molecular Weight:307.3416
Molecular Formula:C16H21NO5
InChIKey:IUQVQBCPGJMDKT-OAHLLOKOSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:354.3997
Molecular Formula:C20H22N2O4
InChIKey:VAYRGDPHWYPECT-BOPFTXTBSA-N
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Compound Information
Molecular Weight:96.106
Molecular Formula:CH4O3S
InChIKey:AFVFQIVMOAPDHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:452.521
Molecular Formula:C21H28N2O7S
InChIKey:JGKLORQAPBNZCH-UNTBIKODSA-N
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Compound Information
Molecular Weight:452.521
Molecular Formula:C21H28N2O7S
InChIKey:JGKLORQAPBNZCH-LMOVPXPDSA-N
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Compound Information
Molecular Weight:740.226
Molecular Formula:C32H48BF4FeP2Rh
InChIKey:CNVIALWRHAVOPH-OMVRSXMXSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:422.31
Molecular Formula:C17H18Cl2N2Ru
InChIKey:ZRWQUSRKVMWVCP-STZRTGCTSA-L
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.335
Molecular Formula:C24H36FeP2
InChIKey:IACTYUFFHOYITF-XTQNZXNBSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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