Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones Catalyzed by a Chiral Phosphoric Acid
Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones Catalyzed by a Chiral Phosphoric Acid
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手性磷酸催化邻甲酰基查耳酮的级联烯丙基硼化/氧化-迈克尔反应对映选择性合成 1,3-二取代 1,3-二氢异苯并呋喃
DOI：
10.1021/acs.joc.7b01856
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发表时间：
2017
影响因子：
3.6
通讯作者：
Huang Yi-Yong
中科院分区：
文献类型：
--
作者：
Yang Xing;Pang Shuai;Cheng Feng;Zhang Yue;Lin Ya-Wei;Yuan Quan;Zhang Fang-Lin;Huang Yi-Yong
首次发现了手性1，3-二取代1，3-二氢异苯并呋喃的手性B酸催化的级联不对称烯丙基硼/氧-迈克尔反应，其产率、非对映选择性比(Dr)和对映体选择性过剩(Ee)分别高达94%、2.5：1和98%。此外，2，3-二烯基硼烷醇酯也应用于级联反应中，取得了较好的催化效果。
The first chiral Brønsted acid-catalyzed asymmetric cascade allylboration/oxo-Michael reaction betweeno-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.