Copper-Catalyzed γ-Selective and Stereospecific Substitution Reaction of Allylic Carbonates with Diboron:  Efficient Route to Chiral Allylboron Compounds

Hajime Ito,* Chika Kawakami, and Masaya Sawamura*;
Division of Chemistry, Graduate School of Science, Hokkaido University, and PRESTO, JST, Sapporo 060-0810, Japan
J. Am. Chem. Soc., 2005, 127 (46), pp 16034–16035
DOI: 10.1021/ja056099x
Publication Date (Web): October 28, 2005
Copyright © 2005 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.

, hajito@sci.hokudai.ac.jp, ; , sawamura@sci.hokudai.ac.jp

Abstract

Abstract Image

A copper-catalyzed γ-selective and stereospecific substitution reaction of allylic carbonates with a diboron reagent affording allylboron compounds is described. Boryl group was selectively introduced at the γ-position of the leaving carbonate group. Functionalized allylboronates that have an acetal, ester, or isolated alkene were prepared. The reaction of optically active allylic carbonates underwent complete α-to-γ chirality transfer with anti-stereochemistry to produce optically active allylboronates having a boron-substituted stereogenic center.

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History

  • Published In Issue November 23, 2005
  • Received September 5, 2005

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