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

Author: Liu Mingshun   Chen Yaqing   Fu Nanyan  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.43, Iss.7, 2013-03, pp. : 1055-1062

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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.