119067-50-4

Upstream product

• 111427-78-2 (S)-3-((S)-2-Benzyloxy-1-hydroxy-ethyl)-2-trimethylsilanyl-dodec-1-en-4-one 
• 111427-78-2 (S)-3-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2-trimethylsilanyl-dodec-1-en-4-one 
• 111427-78-2 (S)-3-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2-trimethylsilanyl-dodec-1-en-4-one 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 111427-76-0 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-2-trimethylsilanyl-undec-1-en-3-ol 
• 112164-80-4 (2S,3R)-2-Benzyloxymethyl-3-[1-trimethylsilanyloxy-1-(1-trimethylsilanyl-vinyl)-nonyl]-oxirane 
• 111427-74-8 1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-nonan-1-one 
• 17049-49-9 octylmagnesium bromide 
• 111427-76-0 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-2-trimethylsilanyl-undec-1-en-3-ol 
• 112164-80-4 (2S,3R)-2-Benzyloxymethyl-3-[1-trimethylsilanyloxy-1-(1-trimethylsilanyl-vinyl)-nonyl]-oxirane 

Relevant academic research and scientific papers

Silicon-Directed Stereoselective Synthesis of 2-vinyl-1,3-diols. Stereo-Divergence with and without the silyl Group Related to the Synthesis of Avenaciolide and Isoavenaciolide

A flexible approach to the stereoisomers of 2-vinyl-1,3-diols via the reduction of 2-vinyl aldols is described.The presence of the TMS group at the α-position of the vinyl group firmly establishes the syn relationship between the newly-formed hydroxyl gro

SYNTHESIS OF 2-VINYL-1,3-DIOLS VIA HIGHLY STEREOSELECTIVE REDUCTION OF 2-VINYL ALDOLS USING TRIMETHYLSILYL STEREO-DIRECTING GROUP

Stereo-defined 2-vinyl-1,3-diols are synthesized by the reduction of aldol derivatives bearing α-trimethylsilylvinyl group at C(2) (LiBEt3H/THF, -78 deg C), which proceeds highly stereoselectively to give 1,2-syn isomer as the sole product.