Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins1

Michael G. Organ,* Jeremy T. Cooper, Lawrence R. Rogers, Fariba Soleymanzadeh, and Timothy Paul
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, Canada M3J 1P3
J. Org. Chem., 2000, 65 (23), pp 7959–7970
DOI: 10.1021/jo001045l
Publication Date (Web): October 21, 2000
Copyright © 2000 American Chemical Society
*

 To whom correspondence should be directed. Voice:  (416)-736-5313. Fax:  (416)-736-5936.

, organ@yorku.ca

Abstract

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Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin β-d-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

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History

  • Published In Issue November 17, 2000
  • Received July 12, 2000

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