Efficient preparation of C2-symmetrical chiral ferrocenyl diols by catalytic enantioselective reduction of diacylferrocenes

Organic Letters

Volumn 4, Issue 19, 2002, Pages 3313-3316

  Sato, Hirohide ^b   Watanabe, Hiroto ^a   Ohtsuka, Yuhki ^a   Ikeno, Taketo ^a   Fukuzawa, Shin Ichi ^b   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

^b CHUO UNIVERSITY   (Japan)

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EID: 0012877734     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266018     Document Type: Article

References (30)

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18. For high stereoselectivity, 60-200 mol % of the oxazaborolidine catalyst was required. Reference 10c.
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23. A duplication effect was reported for the enantioselective reaction of symmetrical compounds. Vigneron, J. P.; Dhaenens, M.; Horeau, A. Tetrahedron 1973, 29, 1055-1059.
24. 13C NMR analysis, and the optical purity was determined by HPLC analysis (Daicel Chiralpak AD-H, 2-propanol/ hexane).
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26. (b) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468.
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29. In the presence of the (R,R)-cobalt complex catalyst, aryl ketones were selectively converted to the corresponding (R)-alcohols in the previous experiments with a few exceptions. See ref 13.
30. Since the prior order of substituents around the asymmetric carbon is hydroxyl > ferrocenyl > phenyl > alkyl > hydrogen, the descriptions for the same enantioselective sense were reversed between the reduction of 1,1′-dibenzoylferrocene and that of acetophenone.