1440422-45-6Relevant academic research and scientific papers
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
Chen, Ming,Roush, William R.
, p. 7551 - 7558 (2013/08/23)
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.
Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl( ddiisopinocampheyl)-crotylborane
Chen, Ming,Roush, William R.
, p. 5468 - 5475 (2013/07/05)
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.
