Article ID Journal Published Year Pages File Type
5216630 Tetrahedron 2014 8 Pages PDF
Abstract

A stereocontrolled approach to functionalized acyclic β2,3-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 stereocontrolled procedure was applied to the synthesis of acylic β2,3-amino acid derivatives functionalized with ester, nitrile, keto, alkyl or arylalkyl groups.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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