Y. Takaya, M. Ogasawara, Tamio Hayashi
Nov 12, 1998
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Journal
Tetrahedron Letters
Abstract
Reaction of 2-alkenyl-1,3,2-benzodioxaboroles, which are readily accessible by hydroboration of alkynes with catecholborane, with α,β-unsaturated ketones in the presence of rhodium(S)-binap catalyst and triethylamine in dioxaneH2O (101) proceeded with high enantioselectivity at 100 °C to give high yields of optically active β-alkenyl ketones of over 90% ee. One pot synthesis of the 1,4-addition product is also successful in the rhodium-catalyzed asymmetric reaction by use of alkenylboranes generated in situ from alkyne and catecholborane.