Dynamic Thermodynamic Resolution:  Solvent Effects, Mechanism, and an Asymmetric 3,4,5-Substituted Benzazepine Synthesis

Yong Sun Park,†‡ Eul Kgun Yum,†§ Amit Basu,† and Peter Beak*†
Department of Chemistry, Roger Adams Laboratory, University of Illinois at UrbanaChampaign, Urbana, Illinois 61801, Department of Chemistry, Konkuk University, Seoul 143-701, Korea, and Department of Chemistry, Chungnam National University, Daejon 305-764, Korea
Org. Lett., 2006, 8 (13), pp 2667–2670
DOI: 10.1021/ol0604015
Publication Date (Web): May 26, 2006
Copyright © 2006 American Chemical Society
†

 Roger Adams Laboratory.

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‡

 Konkuk University.

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§

 Chungnam National University.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, beak@scs.uiuc.edu

Abstract

Abstract Image

The resolution in the lithiation-substitution sequence from 1 to 4−11 in MTBE is shown to be under thermodynamic control in contrast to the previous report of kinetic control in diethyl ether. Diastereomeric equilibration of a soluble complex is shown to be controlling and an asymmetric synthesis of a 3,4,5-substituted benzazepine is reported.

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History

  • Published In Issue June 22, 2006
  • Received February 15, 2006

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