Palladium-Catalyzed Cross-Coupling Reaction of Triorganoindium Reagents with Propargylic Esters

Ricardo Riveiros, David Rodríguez, José Pérez Sestelo,* and Luis A. Sarandeses*
Departamento de Qumica Fundamental, Universidade da Corua, E15071 A Corua, Spain
Org. Lett., 2006, 8 (7), pp 1403–1406
DOI: 10.1021/ol060192o
Publication Date (Web): March 9, 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.

, qfsarand@udc.es

Abstract

Abstract Image

Triorganoindium reagents (R3In) react with propargylic esters under palladium catalysis via an SN2‘ rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R3In (aryl, alkenyl, alkynyl, and methyl). When chiral, nonracemic propargylic esters are employed, the reaction takes place with high anti-stereoselectivity providing allenes with high enantiomeric excess.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue March 30, 2006
  • Received January 23, 2006

Recommend & Share

Related Content

Other ACS content by these authors: