Copper Catalyzed Asymmetric Synthesis of Chiral Allylic Esters

Koen Geurts, Stephen P. Fletcher, and Ben L. Feringa*
Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
J. Am. Chem. Soc., 2006, 128 (49), pp 15572–15573
DOI: 10.1021/ja065780b
Publication Date (Web): November 14, 2006
Copyright © 2006 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.

, B.L.Feringa@rug.nl

Abstract

Abstract Image

The complex derived from Taniaphos ligand 4 and CuBr•Me2S catalyzes the asymmetric addition of Grignard reagents to 3-bromopropenyl esters 1 to provide allylic esters 2 in high yields and high chemio-, regio-, and enantioselectivities. The work demonstrates that allylic asymmetric alkylation (AAA) can be done on substrates bearing a heteroatom at the γ-position. The method is a practical route to chiral, nonracemic allylic alcohols. The use of functionalized substrates 1 or Grignard reagents leads to more complex products 2, which can be further manipulated as demonstrated in conversion to (S)-5-ethyl-2(5H)-furanone 6 and (S)-benzoic acid-cyclopent-2-enyl ester 7.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue December 13, 2006
  • Received August 16, 2006

Recommend & Share

Related Content

Other ACS content by these authors: