1401337-75-4

Upstream product

• 1401338-44-0 (S)-9-benzyl-3-[(2S,3S)-5-(tert-butyldimethylsilyl)-3-(triphenylsilyloxy)-2-methylpent-4-ynoyl]oxazolidin-2-one 
• 1401338-45-1 (2R,3S)-5-(tert-butyldimethylsilyl)-3-(triphenylsilyloxy)-2-methylpent-4-yn-1-ol 
• 149400-42-0 ethyl (2E,4E)-4-methylhexa-2,4-dienoate 
• 1401337-71-0 (2S,3S)-5-(tert-butyldimethylsilyl)-3-(triphenylsilyloxy)-2-methylpent-4-ynal 
• 90083-19-5 3-(tert-butyldimethylsilyl)-2-propynal 
• 86318-61-8 (tert-butyldimethylsilyl)acetylene 
• 376585-98-7 (S)-9-benzyl-3-[(2S,3S)-5-(tert-butyldimethylsilyl)-3-hydroxy-2-methylpent-4-ynoyl]oxazolidin-2-one 

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.