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Letter

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

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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

Org. Lett., 2005, 7 (9), pp 1837–1839

DOI: 10.1021/ol050528e

Publication Date (Web): March 24, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sigman@chem.utah.edu

Abstract

We have identified a new set of stereochemically diverse oxazoline ligands derived from simple amino acids that promote the Cr-catalyzed enantioselective addition of allylic halides to aldehydes in up to 95% ee. The Cr-catalyzed allylation using ligand 1d is rather insensitive to the nature of the allylic bromide (crotyl, allyl, and methallyl) in that >90% ee is observed for all three bromides evaluated in the addition to benzaldehyde.

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Published In Issue April 28, 2005
Received March 10, 2005

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

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

Catalytic Enantioselective Nozaki−Hiyama Allylation Reaction with Tethered Bis(8-quinolinolato) (TBOx) Chromium Complex

Enantiospecific Total Syntheses of Kapakahines B and F

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