Stereochemical Diversity in Chiral Ligand Design: Discovery and Optimization of Catalysts for the Enantioselective Addition of Allylic Halides to Aldehydes

Jae-Young Lee, Jeremie J. Miller, Steven S. Hamilton, and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-085, Email: sigmanchem.utah.edu

J.-Y. Lee, J. J. Miller, S. S. Hamilton, M. S. Sigman, Org. Lett., 2005, 7, 1837-1839.

DOI: 10.1021/ol050528e

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Abstract

Stereochemically diverse oxazoline ligands derived from simple amino acids have been identified that promote the Cr-catalyzed enantioselective addition of allylic halides to aldehydes in up to 95% ee.

see article for more examples

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Design and Synthesis of Modular Oxazoline Ligands for the Enantioselective Chromium-Catalyzed Addition of Allyl Bromide to Ketones

J. J. Miller, M. S. Sigman, J. Am. Chem. Soc., 2007, 129, 2752-2753.

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Key Words

Nozaki-Hiyama Coupling, Homoallylic Alcohols

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ID: J54-Y2005-490