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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 7
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Original Articles

Convenient Synthesis of Adamantyl-Substituted β-Lactams via Uncatalyzed Staudinger Reaction

, &
Pages 1055-1062 | Received 31 Mar 2011, Published online: 07 Jan 2013
 

Abstract

A series of C3-position adamantyl-substituted β-lactams were synthesized via uncatalyzed Staudinger reaction between adamantylketene generated by thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome of the reaction was mainly the formation of trans-products, a result attributed to a two-step mechanism leading to the most stable products.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This work was supported by the National Natural Science Foundation of China (No. 20702005), the Scientific Research Foundation of State Key Laboratory of Elemento-organic Chemistry of Nankai University (No. 0811), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (No. LXKQ0802), and Fujian Provincial Natural Science Foundation of China (No. 2008J0148). We thank Xiao-Qing Zhu from Nankai University and Annette D. Allen from the University of Toronto for spectroscopic measurements and discussion.

Notes

a The isolated yield of trans-6.

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