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Letter

A Facile Stereocontrolled Synthesis of anti-α-(Trifluoromethyl)-β-amino Alcohols

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G. K. Surya Prakash,* Mihirbaran Mandal, Stefan Schweizer, Nicos A. Petasis,* and George A. Olah*

Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661

Org. Lett., 2000, 2 (20), pp 3173–3176

DOI: 10.1021/ol000195f

Publication Date (Web): September 2, 2000

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

, prakash@methyl.usc.edu

Abstract

A short stereocontrolled preparation of anti-α-(trifluoromethyl)-β-amino alcohols is described, involving an initial CF₃ transfer to cinnamaldehyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this methodology to chiral 3,3,3-trifluorolactic aldehyde allowed us to generate an amino alcohol enantioselectively in 92% ee.

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Published In Issue October 05, 2000
Received July 24, 2000

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Letter

A Facile Stereocontrolled Synthesis of anti-α-(Trifluoromethyl)-β-amino Alcohols

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Stereoselective Synthesis of anti-α-(Difluoromethyl)-β-amino Alcohols by Boronic Acid Based Three-Component Condensation. Stereoselective Preparation of (2S,3R)-Difluorothreonine

Highly Stereocontrolled One-Step Synthesis of anti-β-Amino Alcohols from Organoboronic Acids, Amines, and α-Hydroxy Aldehydes

Stereoselective Synthesis of anti-α-(Difluoromethyl)-β-amino Alcohols by Boronic Acid Based Three-Component Condensation. Stereoselective Preparation of (2S,3R)-Difluorothreonine

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