Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology , Wuhan 430070, P.R. China.
J Org Chem. 2017 Oct 6;82(19):10388-10397. doi: 10.1021/acs.joc.7b01856. Epub 2017 Sep 20.
The first chiral Brønsted acid-catalyzed asymmetric cascade allylboration/oxo-Michael reaction between o-formyl chalcones and allylboronate has been successfully discovered, which afforded chiral 1,3-disubstituted 1,3-dihydroisobenzofurans with a yield, diastereoselective ratio (dr) and enantioselective excess (ee) up to 94%, 2.5:1, and 98%, respectively. In addition, 2,3-dienylboronic pinacol ester was also applied into this cascade reaction with good catalytic results.
首例手性 Brønsted 酸催化的不对称级联烯丙基硼化/氧代-Michael 反应已在邻甲酰基查耳酮和烯丙基硼酸酯之间成功发现，该反应以高达 94%的产率、2.5:1 的非对映选择性比（dr）和 98%的对映体过量（ee）提供了手性 1,3-二取代的 1,3-二氢异苯并呋喃。此外，2,3-二烯基硼酸频哪醇酯也应用于该级联反应，催化效果良好。
