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

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journal contribution
posted on 16.03.2006, 00:00 by Taichi Shimada, Masamitsu Yoshioka, Tsutomu Konno, Takashi Ishihara
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.