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Synfacts 2006(2): 0139-0139
DOI: 10.1055/s-2005-924779
DOI: 10.1055/s-2005-924779
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Chiral Fluorous Oxazolidinone Auxiliaries
J. E. Hein, L. M. Geary, A. A. Jaworski, P. G. Hultin*
University of Manitoba, Canada
Further Information
Publication History
Publication Date:
23 January 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200602/lookinside/thumbnails/10.1055-s-2005-924779-1.jpg)
Significance
Fluorous analogues of Evans’ oxazolidinone auxiliaries were synthesized in a short sequence and a relatively large scale (up to 25 g). Lithium fluoroalkyl was added to a Weinreb amide of N-(alkoxycarbonyl)-protected amino acids to give moderate to good yield of the corresponding fluorous ketone. Lewis acid-chelated hydride reduction of the ketones using LiAlH(Ot-Bu)3 afforded the amino alcohol in excellent yield and greater than 99:1 diastereoselectivity. Treatment of the alcohol with NaH gave the corresponding fluorous oxazolidinone auxiliaries.