Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design.

Angew Chem Int Ed Engl

Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin, 4, Ireland.

Published: April 2017

A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.

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http://dx.doi.org/10.1002/anie.201610462DOI Listing

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