1450877-74-3

Upstream product

• 618095-90-2 (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal 
• 1440422-45-6 (4S,5R,6S,7R,8R,Z)-9-((tert-butyldiphenylsilyl)oxy)-4-(dimethyl(phenyl)silyl)-7-methoxy-6,8-dimethylnon-2-en-5-ol 

Relevant academic research and scientific papers

Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl( ddiisopinocampheyl)-crotylborane

The enantiodivergent hydroboration reactions of racemic allenylsilane (±)-4 with (dIpc)2BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5 at -78 C provide (E)-δ-silyl-anti-homoallylic alcohols 6 in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes 20 with (S)-E-5 proceed under Curtin-Hammett control to give anti-β-hydroxylcrotylsilanes 24 as the only products.

Reprint of: Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl( ddiisopinocampheyl)-crotylborane

The enantiodivergent hydroboration reactions of racemic allenylsilane (±)-4 with (dIpc)2BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5 at -78 C provide (E)-δ-silyl-anti-homoallylic alcohols 6 in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes 20 with (S)-E-5 proceed under Curtin-Hammett control to give anti-β-hydroxylcrotylsilanes 24 as the only products.