Chemistry: A European Journal 2012-10-01

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ-butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides.

Huai-Long Teng, He Huang, Chun-Jiang Wang

Index: Chemistry 18(40) , 12614-8, (2012)

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Abstract

Spiro(γ-butyrolactam-γ-butyrolactone): a route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid.Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.