Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles:  Application to the Enantioselective Synthesis of Indolodioxane U86192A

Junghyun Chae and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts, 02139
J. Org. Chem., 2004, 69 (10), pp 3336–3339
DOI: 10.1021/jo035819k
Publication Date (Web): April 20, 2004
Copyright © 2004 American Chemical Society
*

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

, sbuchwal@mit.edu

Abstract

Abstract Image

A novel approach to the selective preparation of 4-bromoindoles was developed via Pd(OAc)2/rac-BINAP catalytic reactions. A variety of 4,6-dibromoindoles were transformed to 4-bromoindoles with high regioselectivity. This methodology, along with C−N and C−O bond-forming reactions developed in our laboratory, was applied to the enantioselective synthesis of indolodioxane U86192A, an antihypertensive agent.

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History

  • Published In Issue May 14, 2004
  • Received December 15, 2003

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