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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, Email: christopher_setobrown.edu

C. M. Sprout, M. L. Richmond, C. T. Seto, J. Org. Chem., 2005, 70, 7408-7417.

DOI: 10.1021/jo051342w (free Supporting Information)


Abstract

Various N-acylethylenediamine-based ligands were screened as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes. The optimized ligand was found to catalyze the formation of (E)-allylic alcohols with high enantioselectivities for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.

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Key Words

Alcohols, Vinylboranes, Allylic Alcohols


ID: J42-Y2005-1300