Journal of the American Chemical Society 2010-11-10

Asymmetric bromolactonization using amino-thiocarbamate catalyst.

Ling Zhou, Chong Kiat Tan, Xiaojian Jiang, Feng Chen, Ying-Yeung Yeung

Index: J. Am. Chem. Soc. 44th ed., 132 , 15474-15476, (2010)

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Abstract

A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.