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Issue 60, 2017
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Direct stereoselective construction of cyclopropane α-amino acid with contiguous quaternary centers via [4 + 2] annulation reaction

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Abstract

A direct diastereoselective synthetic approach to useful cyclopropane α-amino acid was established via base-promoted [4 + 2] annulations between o-aminobenzaldehydes and alkyl 2-aroyl-1-chlorocyclopropanecarboxylates. The annulation reaction proceeded quickly under mildly basic conditions, affording α-aminocyclopropanecarboxylic acid derivatives in moderate to excellent yields with high diastereoselectivities (up to 19 : 1).

Graphical abstract: Direct stereoselective construction of cyclopropane α-amino acid with contiguous quaternary centers via [4 + 2] annulation reaction

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Supplementary files

Article information


Submitted
09 Jun 2017
Accepted
13 Jul 2017
First published
02 Aug 2017

This article is Open Access

RSC Adv., 2017,7, 38077-38080
Article type
Paper

Direct stereoselective construction of cyclopropane α-amino acid with contiguous quaternary centers via [4 + 2] annulation reaction

J. Hu, Y. Xu, D. Liu, B. Sun, Y. Yi and F. Zhang, RSC Adv., 2017, 7, 38077
DOI: 10.1039/C7RA06465A

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