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Synfacts 2006(2): 0139-0139  
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

Contributor(s): Mark Lautens, Y. Eric Fang
J. E. Hein, L. M. Geary, A. A. Jaworski, P. G. Hultin*
University of Manitoba, Canada
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Publication History

Publication Date:
23 January 2006 (online)

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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.