Chiral Organometallic Reagents, VIII. On the Configurational Stability of α‐Hetero‐Substituted Benzyllithium Compounds
- 24 July 1992
- journal article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1992 (7) , 725-730
- https://doi.org/10.1002/jlac.1992199201122
Abstract
A test based on kinetic resolution was applied to probe the configurational stability of various α‐substituted benzyllithium compounds 1. It was found that the trimethylsilyl‐ (1b), phenylsulfenyl‐ (1c), and the phenylselenyl‐substituted (1d) benzyllithium compounds enantiomerized more rapidly than they added to the chiral aldehyde 6. In contrast, the carbamoyloxy‐ (1e), (16), and the phenylsulfonyl‐substituted (1g) benzyllithium compounds were found to be configurationally stable on the time scale set by their addition to the aldehyde 6.Keywords
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