## Abstract α‐Methylbenzyllithium (6) should possess either central or planar chirality. The rate of enantiomerization of 6 at — 78^°^C was found to be faster than its addition to the amide 7, the ketone 8, or to the aldehyde 10, according to a test based on kinetic resolution. The benzyllithium co
Chiral Carbanions, 1. Configurational Stability and Reactions of α-Acyloxy-Substituted α-Methylbenzyllithium Compounds
✍ Scribed by Hammerschmidt, Friedrich ;Hanninger, Achim
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 1995
- Tongue
- English
- Weight
- 968 KB
- Volume
- 128
- Category
- Article
- ISSN
- 0009-2940
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## 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
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The title compound, 6, was generated by stereospecific chlorides leads to partial racemization due to competing front face attack. Semiempirical calculations point to an increased deprotonation of the optically active carbamate 5 with secbutyllithium/TMEDA and proved to be configuratively degree of