Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines

作者:Alam Rauful; Das Arindam; Huang Genping; Eriksson Lars; Himo Fahmi; Szabo Kalman J*
来源:Chemical Science, 2014, 5(7): 2732-2738.
DOI:10.1039/c4sc00415a

摘要

Direct allylboration of various acyclic and cyclic aldimine, ketimine and indole substrates was performed using allylboronic acids. The reaction proceeds with very high anti-stereoselectivity for both E and Z imines. The allylboroxines formed by dehydration of allylboronic acids have a dual effect: promoting E/Z isomerization of aldimines and triggering the allylation by efficient electron withdrawal from the imine substrate.

  • 出版日期2014