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Synlett 1997; 1997(SI): 449-450
DOI: 10.1055/s-1997-6144
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Stereoselective Conjugate Addition of an α-Sulfinyl Carbanion to α,β-Unsaturated Esters: Asymmetric Synthesis of Cycloalkanecarboxylates

Takeshi Toru* , Shuichi Nakamura, Hirofumi Takemoto, Yoshio Ueno
  • *Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466, Japan, Fax 52-735-5247; E-mail toru@ach.nitechn.ac.jp
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Publication Date:
31 December 2000 (online)

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The reaction of lithiated (R)-2-(trimethylsilyl)ethyl p-tolyl sulfoxide 1 with α,β-unsaturated esters gives 1,4-conjugate addition products as single stereoisomers, whereas the reaction of 1 with 4-, 6-, or 7-haloalkenoates affords cyclopropane-, cyclopentane- or cyclohexanecarboxylates, respectively, with high stereoselectivity.

α-sulfinyl carbanion - chiral sulfoxide - conjugate addition - chiral cycloalkanes