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Synlett 1999; 1999(10): 1600-1602
DOI: 10.1055/s-1999-2885
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Stereoselective 2-Hydroxy-1,2,2-triphenylethyl Propionate-Based Aldol Additions to Ketones

Manfred Braun* , Brigitte Mai, Daniel M. Ridder
  • *Institut für Organische und Makromolekulare Chemie, Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany; Fax + 49 21 18 11 30 85; E-mail: braunm@uni-duesseldorf.de
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Publication Date:
31 December 1999 (online)

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The TiCl4-mediated reaction of enone 3 with the silyl ketene acetal 2 derived from (R)-propionate 1 occurs in a stereoselective manner. The major aldol adduct 4, whose configuration was proven by an X-ray structure analysis of 6, affords the enantiomerically pure carboxylic acid 5 upon hydrolysis.

asymmetric synthesis - aldol reaction - ketones - titanium - tertiary alcohols