Stereoselective hydroxyalkylations of (S)??2??azetidinecarboxylic acid

D Seebach, T Vettiger, HM Müller…

Index: Seebach, Dieter; Vettiger, Thomas; Mueller, Hans-Martin; Plattner, Dietmar A.; Petter, Walter Liebigs Annalen der Chemie, 1990 , # 7 p. 687 - 695

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Citation Number: 19

Abstract

Abstract The enolate generated from S-phenyl (S)-1-benzyl-2-azetidinecarbothioate is converted into racemic products 2 by treatment with electrophiles. The bicyclic oxazolidinone derivative 12 has been prepared from trimethylsilyl (S)-1-(trimethylsilyl)-2- azetidinecarboxylate (11) and pivalaldehyde without racemization. Addition of 12 to aldehydes and hydrolysis gives the products 13 ah. The structure of the adduct 13 h from ...