Enantioselective cis-β-lactam synthesis by intramolecular C–H functionalization from enoldiazoacetamides and derivative donor–acceptor cyclopropenes

Xinfang Xu; Yongming Deng; David N. Yim; Peter Y. Zavalij; Michael P. Doyle

doi:10.1039/C4SC03991B

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Enantioselective cis-β-lactam synthesis by intramolecular C–H functionalization from enoldiazoacetamides and derivative donor–acceptor cyclopropenes†

Xinfang Xu,*^a Yongming Deng,^b David N. Yim,^b Peter Y. Zavalij^b and Michael P. Doyle*^b

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* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
E-mail: xinfangxu@suda.edu.cn
Tel: +86 0512 65883612

^b Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA
E-mail: mdoyle3@umd.edu

Abstract

β-Lactam derivatives are produced through intermediate donor–acceptor cyclopropene intermediates in high yield, exclusive cis-diastereoselectivity, and high enantiocontrol in a chiral dirhodium carboxylate catalyzed intramolecular C–H functionalization reaction of enoldiazoacetamides.

This article is part of the themed collection: SU 120: Celebrating 120 Years of Soochow University

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DOI: https://doi.org/10.1039/C4SC03991B
Article type: Edge Article
Submitted: 23 Dec 2014
Accepted: 27 Jan 2015
First published: 28 Jan 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2015,6, 2196-2201

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Enantioselective cis-β-lactam synthesis by intramolecular C–H functionalization from enoldiazoacetamides and derivative donor–acceptor cyclopropenes

X. Xu, Y. Deng, D. N. Yim, P. Y. Zavalij and M. P. Doyle, Chem. Sci., 2015, 6, 2196 DOI: 10.1039/C4SC03991B

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Chemical Science

Enantioselective cis-β-lactam synthesis by intramolecular C–H functionalization from enoldiazoacetamides and derivative donor–acceptor cyclopropenes†

Abstract

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Enantioselective cis-β-lactam synthesis by intramolecular C–H functionalization from enoldiazoacetamides and derivative donor–acceptor cyclopropenes

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