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Synlett 1998; 1998(6): 607-608
DOI: 10.1055/s-1998-1746
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Conformational Control in Proton Sources for Enantioselective Protonation of Samarium Enolate Derived From α-Methoxy-Substituted Ketones

Koichi Mikami* , Makoto Yamaoka, Akihiro Yoshida
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan
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Publication Date:
31 December 2000 (online)

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High enantioselectivity is achieved in the asymmetric protonation of samarium enolate, regioselectively generated by SmI2-mediated reduction of 2-methoxy-substituted cyclohexanones using achiral diamine- or pro-atropisomeric 2,2′-biphenol-derived chiral diols as proton sources by virtue of the conformational control.

Samarium enolate - enantioselective protonation - conformational control - achiral diamine - achiral pro-atropisomeric biphenol

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