245073-29-4

Upstream product

• 87696-33-1 (S)-2-(O-tert-butyldiphenylsilyloxy)propanal 
• 187590-50-7 (S) 4-(tert-butyldimethylsilyloxy)-3-pentanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 188660-03-9 (S)-2-(tert-butyl-dimethyl-silanyloxy)-N-methoxy-N-methyl-propionamide 

Downstream Products

• 245073-31-8 (2S,4R,5R,6S)-6-tert-butyldiphenylsilyloxy-2,5-dihydroxy-4-methyl-3-pentanone 

Relevant academic research and scientific papers

Stereoselective titanium-mediated aldol reactions of (S)-2-tert-butyldimethylsilyloxy-3-pentanone

Titanium-mediated aldol reactions based on (S)-2-tert-butyldimethylsilyloxy-3-pentanone, a lactate-derived chiral ketone, provide the corresponding 2,4-syn-4,5-syn adducts in high yields and diastereomeric ratios with a wide array of achiral and chiral aldehydes. Furthermore, spectroscopic studies of intermediates involved in the process have permitted to propose a mechanism that accounts for the experimental results.

Reaction of chiral titanium Z-enolates with chiral α-silyloxy aldehydes. Syntheses of NFX-2 and antimycinone

Titanium-mediated aldol reactions of 1 and (S)-2-tert- butyldiphenylsilyloxy aldehydes (matched pair) afford syn Felkin diastereomers in excellent yield and absolute stereochemical control. Having established that chain length does not affect the yield of the titanium aldol reactions, we have been able to achieve short, high yielding and enantioselective syntheses of NFX-2 and Antimycinone.