1. The stereochemistry of hippurate alkylation
- Author
-
E. Jay Kiser, Zhigang Tian, and John M. McIntosh
- Subjects
chemistry.chemical_compound ,Benzyl bromide ,chemistry ,Stereochemistry ,Yield (chemistry) ,Organic Chemistry ,Cyclohexanol ,Stereoselectivity ,General Chemistry ,Alkylation ,Catalysis ,Phenylalanine derivatives - Abstract
Alkylation of the hippurate esters of trans 2-(p-substituted phenyl)cyclohexanol with benzyl bromide affords phenylalanine derivatives in high chemical yield. The reaction stereoselectivity varies from 20 to >98% depending on the aromatic group in the cyclohexyl auxiliary. A model that correctly predicts the sense of the induction is proposed.
- Published
- 1998
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