A straightforward synthesis of both enantiomers of allo-norcoronamic acids and allo-coronamic acids, by asymmetric Strecker reaction from alkylcyclopropanone …

A Fadel, A Khesrani

Index: Fadel, Antoine; Khesrani, Aballache Tetrahedron Asymmetry, 1998 , vol. 9, # 2 p. 305 - 320

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Citation Number: 43

Abstract

Methylcyclopropanone hemiacetal (2S)-3a underwent the asymmetric Strecker reaction induced by a chiral amine to provide a useful synthesis of enantiomerically pure (1R, 2S)-(+)- allo-norcoronamic acid 1 in good yield and high enantiomeric excess. From racemic alkyl hemiacetal (±)-3, the same methodology also constituted a useful way to prepare both (+)-1 and (−)-1 and (+)-allo-coronamic acid 2 and its antipode (−)-2 with good yield and high ...