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Stereocontrolled transformation of cyclohexene b-amino esters into syn- or anti-difunctionalized acyclic b2,3-amino acid derivatives

Cherepanova, Maria and Kiss, Loránd and Fülöp, Ferenc (2014) Stereocontrolled transformation of cyclohexene b-amino esters into syn- or anti-difunctionalized acyclic b2,3-amino acid derivatives. TETRAHEDRON, 70. pp. 2515-2522. ISSN 0040-4020

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Abstract

A stereocontrolled approach to functionalized acyclic b2,3-amino acid derivatives was accomplished from cis- or trans-2-aminocyclohexenecarboxylates derived from bicyclic b-lactam regioisomers. The transformations were based on oxidative ring cleavage through the ring CeC double bond of the cyclohexene b-amino esters, followed by functionalization of the dialdehyde intermediates with different phosphoranes. This stereospecific and stereocontrolled procedure was applied to the synthesis of acylic b2,3-amino acid derivatives functionalized with ester, nitrile, keto, alkyl or arylalkyl groups.

Item Type: Article
Uncontrolled Keywords: Ring cleavage, Oxidation, Wittig reaction, Amino acids, Functionalization
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dr Loránd Kiss
Date Deposited: 11 Sep 2014 12:25
Last Modified: 11 Sep 2014 12:25
URI: http://real.mtak.hu/id/eprint/14726

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