A Positional Scanning Approach to the Discovery of Dipeptide-Based Catalysts for the Enantioselective Addition of Vinylzinc Reagents to Aldehydes

Christopher M. Sprout, Meaghan L. Richmond, and Christopher T. Seto*
Department of Chemistry, Brown University, 324 Brook Street Box H, Providence, Rhode Island 02912
J. Org. Chem., 2005, 70 (18), pp 7408–7417
DOI: 10.1021/jo051342w
Publication Date (Web): August 6, 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.

, christopher_seto@brown.edu

Abstract

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A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.

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History

  • Published In Issue September 02, 2005
  • Received June 29, 2005

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