Phosphine-catalyzed asymmetric synthesis of beta-lactones from arylketoketenes and aromatic aldehydes.

Org Lett

Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.

Published: April 2010

In this paper, the development of a chiral phosphine-catalyzed formal [2 + 2] cycloaddition of aldehydes and ketoketenes that provides access to a variety of highly substituted beta-lactones (14 examples) is reported. The BINAPHANE catalytic system displays excellent enantioselectivity (seven examples with ee >or=90%) and high diastereoselectivity favoring formation of the trans-diastereomer (nine examples with dr >or=90:10).

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Source
http://dx.doi.org/10.1021/ol100075mDOI Listing

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