Abstract
The hydroboration of cycloalka-1,3-dienes (CnH2n–4, n= 6, 7 and 8) with diisopinocampheylborane, (dIpc2BH or IIpc2BH) at –25°C provides highly enantiomerically pure B-(cycloalk-2-enyl)diisopinocampheylboranes, I or dIpc2BCnH2n–3( 93% ee). Surprisingly, these allylic borane derivatives retain their stereochemical integrity at –25 °C although such compounds are capable of undergoing racemization through rapid allylic rearrangements. Furthermore, the B-(cycloalk-2-enyl)diisopino-campheylboranes achieve allylborations of aldehydes at –78 °C and afford 1 -(cycloalk-2-enyl)alkan-1- ols in 90–95% ee and 100%syn-diastereoselectivity.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
