1025872-38-1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 312538-66-2 (S)-2-tert-Butyldimethylsilyloxy-3-decanone 
• 188659-92-9 (S)-2-(tert-butyldimethylsilyloxy)-N,N-tetramethylenepropanamide 
• 21369-64-2 n-hexyllithium 
• 108-12-3 isopentanoyl chloride 
• 245073-33-0 (2S,4R,5R,6S)-2-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxy-4-hexyl-5-hydroxy-3-heptanone 

Relevant academic research and scientific papers

Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products

Chiral α-silyloxy ketones participate in highly stereoselective TiCl4-mediated aldol reactions that afford diastereomerically pure syn-syn adducts in high yield irrespective of the R1 and R 2 substituents flanking the carbonyl or the silicon protecting group. Further manipulation of the resulting aldol adducts provide in a straightforward manner highly functionalized fragments that facilitate the synthesis of natural products.

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.