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Chiral synthesis via organoboranes. 24. B-allylbis(2-isocaranyl)borane as a superior reagent for the asymmetric allylboration of aldehydes

✍ Scribed by Brown, Herbert C.; Randad, Ramnarayan S.; Bhat, Krishna S.; Zaidlewicz, Marek; Racherla, Uday S.

Book ID: 120008228
Publisher: American Chemical Society
Year: 1990
Tongue: English
Weight: 508 KB
Volume: 112
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00162a047

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Chiral synthesis via organoboranes. 25.

Chiral synthesis via organoboranes. 25. B-(Z and E)-crotylbis-(2-isocaranyl)boranes as valuable reagents for the asymmetric crotylboration of aldehydes

✍ Herbert C. Brown; Ramnarayan S. Randad 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 351 KB

The asymmetric crotylboration of representative aldehydes, RCHO (R = Me, Et-), with B-[Z and El-crotylbis@isocaranyl)boranes (4 and 5) proceeds with remarkably high enantioselectivity (>94-98% ee) and diastereoselectivity (>99% de) at -78 Oc in ethyl ether.