Tetrahedron: Asymmetry

Rh (II)-catalyzed asymmetric cyclopropenation of propargyl derivatives; synthesis of cyclopropene-and cis-cyclopropane-amino acids

P Müller, H Imogaı̈

Index: Mueller, Paul; Imogai, Hassan Tetrahedron Asymmetry, 1998 , vol. 9, # 24 p. 4419 - 4428

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Citation Number: 31

Abstract

The [Rh2 {(2S)-mepy} 4]-catalyzed cyclopropenation of propargylamines carrying two carboxyl or sulfonyl protecting groups with ethyl diazoacetate proceeds in high yield and with enantioselectivities in the range of 90–> 97% ee. Selective deprotection of the TEOC- derivative afforded ethyl 2-aminomethylcycloprop-2-ene-1-carboxylate which was converted to several analogs of γ-aminobutyric acid (GABA) containing the cyclopropene or ...