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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

✍ Scribed by Alberto Avenoza; Carlos Cativiela; Miguel París; Jesús M. Peregrina

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 596 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00174-n

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✦ Synopsis

Optically active cis-, 8a and 8b, and trans-l-aminomethyl-2-phenylcyclohexane-1carboxylic 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 l]-amino acids led to the corresponding ~ctdisubstituted-[3-1actams 10a, 10b, lla and lib in enantiomerically pure forms.

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