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Synthesis of a new type of conformationally constrained α,α-disubstituted-β-amino acids and β-lactams in enantiomerically pure form

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
6
Identifiers
DOI: 10.1016/0957-4166(95)00174-n

Abstract

Abstract Optically active cis-, 8a and 8b, and trans-1-aminomethyl-2-phenylcyclohexane-1-carboxylic acids, 9a and 9b, were obtained starting from 1,3-butadiene using Diels-Alder cycloadditions with chiral (E)-2-cyanocinnamates as key steps and following a protocol of stereocontrolled reactions. Subsequent cyclization of these conformationally constrained β-amino acids led to the corresponding α,α-disubstituted-β-lactams 10a, 10b, 11a and 11b in enantiomerically pure forms.

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