Journal of the Chemical Society. Perkin transactions I p. 271 - 282 (1995)
Update date:2022-08-03
Topics:
Morikawa, Tsutomu
Washio, Yoshiaki
Harada, Susumu
Hanai, Ryo
Kayashita, Takashi
et al.
Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to γ-oxy-α,β-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-O-isopropylideneglyceraldehyde 3, respectively.The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave β-addition products with syn-stereoselectivity (syn:anti = 8.6:1 - syn only).The reactions of (E)-2 were non-stereoselective.Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.
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