Highly Stereoselective TiCl4-Catalyzed Evans−Aldol and Et3Al-Mediated Reformatsky Reactions. Efficient Accesses to Optically Active s yn- or a nti-α-Trifluoromethyl-β-hydroxy Carboxylic Acid Derivatives

The TiCl4-catalyzed Evans−aldol reaction of optically active 3,3,3-trifluoropropanoic imide gave the non-Evans syn product stereoselectively, whereas the Reformatsky reaction of 2-bromo-3,3,3-trifluoropropanoic imide in the presence of Et3Al led to the Evans anti product. These new approaches enable...

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Bibliographic Details
Published in:Organic letters 2006-03, Vol.8 (6), p.1129-1131
Main Authors: Shimada, Taichi, Yoshioka, Masamitsu, Konno, Tsutomu, Ishihara, Takashi
Format: Article
Language:English
Online Access:Get full text
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Summary:The TiCl4-catalyzed Evans−aldol reaction of optically active 3,3,3-trifluoropropanoic imide gave the non-Evans syn product stereoselectively, whereas the Reformatsky reaction of 2-bromo-3,3,3-trifluoropropanoic imide in the presence of Et3Al led to the Evans anti product. These new approaches enabled us to synthesize all stereoisomers of trifluoromethylated aldol products for the first time.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0531435