Tetrahedron letters

Optically active oxazolidinones as Michael donors for the short and efficient synthesis of β-amino acids containing a cyclopropane ring

M Es-Sayed, C Gratkowski, N Krass, AI Meyers…

Index: Es-Sayed, Mazen; Gratkowski, Corinna; Krass, Norbert; Meyers, Albert I.; De Meijere, Armin Tetrahedron Letters, 1993 , vol. 34, # 2 p. 289 - 292

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Citation Number: 24

Abstract

Abstract The Michael addition of optically active 3, 4-diphenyloxazolidinone 5 to 2′- substituted 2-chloro-2-cyclopropylideneacetates yields 2′-substituted 2-cyclopropyl-1′-(2- oxo-3, 4-diphenyloxazolidin-3-yl) acetates 6-R with excellent trans-selectivity, which upon reductive dehalogenation and subsequent hydrogenolysis give free 2-(1′-amino- cyclopropyl) acetic acids 9.