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Updated: Jul 8, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Super silyl group for a sequential diastereoselective aldol-polyhalomethyllithium addition reaction
Matthew B Boxer1, Hisashi Yamamoto
1Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Abstract:
The super silyl group governs high diastereoselectivity and yields for a sequential aldol-polyhalomethyllithium addition reaction. This unique silyl group is necessary to obtain the diastereoselectivities associated with this sequential reaction, capable of generating two new stereocenters. Alpha-polyhalomethylcarbinols are generated with the simple and inexpensive dihalomethanes and trihalomethanes.
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