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Isopinocampheylbromoborane, a new promising reagent for the asymmetric hydroboration of prochiral alkenes

✍ Scribed by Ulhas P. Dhokte; Herbert C. Brown

Book ID: 104255909
Publisher: Elsevier Science
Year: 1996
Tongue: French
Weight: 253 KB
Volume: 37
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02118-1

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✦ Synopsis

A new promising in situ generated hydroborating agent, isopinocampheylbromoborane (IpcBHBr), achieves the asymmetric hydroboration of representative prochiral alkenes in pentane at lower temperatures, even at -78 °C, than has been possible with isopinocampheylborane (IpcBH2) and isopinocampheylchloroborane.EE (IpcBHC1.EE) reagents, usually in higher enantioselectivities than previously achieved. This is first time that the asymmetric hydroboration of prochiral alkenes with an ot-pinene-derived borane reagent (IpcBHBr) has been achieved at such low temperature, -78 °C, in a relatively short time, 4-6 h.

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