501012-88-0

Upstream product

• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 90083-19-5 3-(tert-butyldimethylsilyl)-2-propynal 
• 130835-27-7 (R)-4-benzyl-3-(prop-2-enoyl)-1,3-oxazolidin-2-one 
• 86318-61-8 (tert-butyldimethylsilyl)acetylene 

Downstream Products

• 501012-89-1 (4R)-benzyl-3-[5-(tert-butyldimethylsilyl)-(3R)-methoxy-(2R)-methyl-4-pentynyl]-oxazolidin-2-one 
• 1401338-36-0 (2R,3R)-5-(tert-butyldimethylsilyl)-N-methoxy-3-(4-methoxybenzyloxy)-N,2-dimethylpent-4-ynamide 
• 1401337-67-4 C₂₀H₃₀O₃Si 
• 902132-82-5 C₃₄H₄₂O₃Si 
• 902132-74-5 C₂₅H₂₄O₂ 
• 902132-73-4 C₃₁H₃₈O₂Si 

Relevant academic research and scientific papers

Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products. The Royal Society of Chemistry 2012.

Synthesis of cystothiazole E and formal syntheses of cystothiazoles A and C by Pd0-catalyzed cross-coupling reactions

The synthesis of the naturally occurring bithiazole (+)-cystothiazole E (1e) is described starting from oxazolidinone 2. It proceeded in 10 steps and an overall yield of 37%. The key reaction of the sequence was a Suzuki cross-coupling between bromobithia