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Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3, 4-tetrahydroisoquinolines.

作者信息

Philippe N, Levacher V, Dupas G, Quéguiner G, Bourguignon J

机构信息

Laboratoire de Chimie Organique Fine et Hétérocyclique UPRES-A 6014, IRCOF-INSA, rue Tesnières B.P 08, F-76131 Mont Saint Aignan Cedex, France.

出版信息

Org Lett. 2000 Jul 27;2(15):2185-7. doi: 10.1021/ol0057939.

DOI:10.1021/ol0057939
PMID:10930239
Abstract

Highly diastereoselective protonation of chiral lactam enolates of 4-substituted-1,4-dihydroisoquinolin-3-ones is reported. Protonation and alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity. This diastereoselective protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.

摘要

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