249612-80-4

Upstream product

• 135822-23-0 (R)-1-(trimethylsilyloxy)-1-<1,2,2-triphenyl-2-(trimethylsilyloxy)ethoxy>-1-propene 
• 3102-33-8 trans-3-penten-2-one 
• 135789-37-6 (R)-2-hydroxy-1,2,2-triphenylethyl propionate 

Downstream Products

• 95061-46-4 (R)-1,1,2-triphenylethane-1,2-diol 

Relevant academic research and scientific papers

Reaction of 2-hydroxy-1,2,2-triphenylethyl propionate with non-activated ketones and enones: Stereoselective aldol and Michael addition

The TiCl4-mediated Mukaiyama-type reaction of the silyl ketene acetal 2, derived from (R)-propionate 1, with the ketones 3a-d occurs in a stereoselective manner. The aldol product 4c is obtained from the enone 3c, whereas the homologous compound 3d undergoes a 1,4 addition and leads to the keto ester 5. The configurations of the deprotected aldol adduct 6 (obtained from 3c) and the Michael product 5 are determined by crystal structure analyses. The diastereomerically and enantiomerically pure esters 4a-c, 5, and 6, as well as the carboxylic acid 7 and the diol 8, containing two or three contiguous stereogenic carbon centers, are prepared. The enantiomerically pure compounds 7 and 8 result from the cleavage of the chiral auxiliary reagent 1,1,2-triphenyl-1,2-ethanediol, which can be recovered.

Stereoselective 2-hydroxy-1,2,2-triphenylethyl propionate-based aldol additions to ketones

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.