Toward a potential total synthesis of gelsemine: A regioselective hydroboration directed by a remote olefin

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Duration: 3 min 30 s
Description: Hydroboration of bicyclo[3.2.1]octa-2,6-diene derivatives occurred exclusively on one olefin, and within this olefin, remarkable regioselective addition of boron to one carbon terminus was observed. This regioselectivity was significantly improved with more electrophilic hydroborating agents. The regioselectivity is attributed to the directive effect of a remote olefin.
Fay Ng; Pauline Chiu; Samuel J. Danishefsky
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