Article
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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| Published in | Canadian journal of chemistry Vol. 76; no. 2; pp. 147 - 151 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
01.02.1998
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| Online Access | Get full text |
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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.Key words: enolate conformation, pi-stacking, 2-phenylcyclohexanol, chiral auxiliary. |
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| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v97-223 |