Chiral synthesis via organoboranes. 35. Simple procedures for the efficient recycling of the terpenyl chiral auxiliaries and convenient isolation of the homoallylic alcohols in asymmetric allyl- and crotylboration of aldehydes

Chiral synthesis VIA organoboranes. 26.

Chiral synthesis VIA organoboranes. 26. An efficient synthesis of isoprenyl derivatives of borane - valuable reagents for the isoprenylboration of aldehydes. A convenient route to both enantiomers of ipsenol and ipsdienol in high optical purity

✍ Herbert C. Brown; Ramnarayan S. Randad 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 788 KB

Preparahon of B-isoprenyldialkylboranes is achieved by adopting the Brandsma modification of the Schlosser procedure, namely metallation of isoprene with potassium 2,2,5,5tetramethylpiperidide followed by sequential treatment with B-methoxydialkylborane and boron trifluoride-etherate. These reagent