Chiral Organometallic Reagents, VIII. On the Configurational Stability of α‐Hetero‐Substituted Benzyllithium Compounds

Abstract

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 .