Tetrahedron

Stereocontrolled transformation of cyclohexene β-amino esters into syn-or anti-difunctionalized acyclic β 2, 3-amino acid derivatives

M Cherepanova, L Kiss, F Fülöp

Index: Cherepanova, Maria; Kiss, Lorand; Fueloep, Ferenc Tetrahedron, 2014 , vol. 70, # 15 p. 2515 - 2522

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Citation Number: 5

Abstract

Abstract A stereocontrolled approach to functionalized acyclic β 2, 3-amino acid derivatives was accomplished from cis-or trans-2-aminocyclohexenecarboxylates derived from bicyclic β-lactam regioisomers. The transformations were based on oxidative ring cleavage through the ring C–C double bond of the cyclohexene β-amino esters, followed by functionalization of the dialdehyde intermediates with different phosphoranes. This stereospecific and ...