Journal of the American Chemical Society p. 2389 - 2392 (1990)
Update date:2022-08-17
Topics:
Brown, Herbert C.
Randad, Ramnarayan S.
Bhat, Krishna S.
Zaidlewicz, Marek
Racherla, Uday S.
Hydroboration of (+)-2-carene, readily available via the base-induced isomerization of (+)-3-carene, provides bis(2-isocaranyl)borane, which can be readily transformed into B-allylbis(2-isocaranyl)borane (2-dICr2BAll). This new reagent undergoes asymmetric allylboration with a variety of aldehydes and affords the corresponding homoallylic alcohols in 94-99% ee. The enantioselectivities realized with this reagent are significantly higher than those realized with the previously explored reagents, B-allyldiisopinocampheylborane (dIpc2Ball) and B-allylbis(4-isocaranyl)borane (4-dIcr2BAll).
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