The stereochemistry of hippurate alkylation

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...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 76; no. 2; pp. 147 - 151
Main Authors McIntosh, JM, Kiser, EJ, Tian, ZG
Format Journal Article
LanguageEnglish
Published OTTAWA CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS 01.02.1998
Canadian Science Publishing NRC Research Press
Subjects
Bromine
Chemistry
Chemistry, Multidisciplinary
Esters
Physical Sciences
Science & Technology
Stereochemistry
enolate conformation
pi-stacking
2-phenylcyclohexanol
chiral auxiliary
ASYMMETRIC INDUCTION
AMINO-ACIDS
DIASTEREOSELECTIVITY
ESTERS
CHIRAL AUXILIARIES
CYCLIZATION
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Summary: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.
ISSN:0008-4042
1480-3291
DOI:10.1139/cjc-76-2-147