Asymmetric Catalysis of Nozaki−Hiyama Allylation and Methallylation with A New Tridentate Bis(oxazolinyl)carbazole Ligand

Masahiro Inoue, Takahiro Suzuki, and Masahisa Nakada*
Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
J. Am. Chem. Soc., 2003, 125 (5), pp 1140–1141
DOI: 10.1021/ja021243p
Publication Date (Web): January 14, 2003
Copyright © 2003 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.

, mnakada@waseda.jp

Abstract

Abstract Image

This work describes the development of a new tridentate ligand effective for the asymmetric catalysis of Nozaki−Hiyama allylation and methallylation. Various aldehydes were allylated or methallylated with good enantioselectivity (86−96%), and a key intermediate of calcitriol lactone synthesis was also obtained with excellent diastereoselectivity (97% de, 91%). The enantioselective reaction catalyzed by this Cr−ligand complex is applicable to a broad range of aldehydes and has great potential for natural product synthesis. Another remarkable feature of this ligand is the stability of the Cr−ligand complex which was recovered after the enantioselective reaction and recycled twice without diminishing the enantioselectivity and yield.

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History

  • Published In Issue February 05, 2003
  • Received October 3, 2002

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