Highly Stereoselective Diels-Alder Reactions Catalyzed by Diboronate Complexes

被引：0
|
作者：
Li, Yuan-He [1 ,2 ,3 ]
Zhang, Su-Lei [1 ,2 ,3 ]
Lu, Yong [1 ,2 ,3 ]
Xiao, Bo [4 ]
Sun, Tian-Yu [4 ]
Xu, Qian-Qian [1 ,2 ,3 ]
Chen, Jia-Hua [1 ,2 ,3 ]
Yang, Zhen [1 ,2 ,3 ,5 ,6 ]
机构：
[1] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[2] Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[3] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
[4] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China
[5] Shenzhen Bay Lab, Shenzhen 518055, Peoples R China
[6] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Key Lab Chem Genom, Shenzhen 518055, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 33期
基金：
美国国家科学基金会;
关键词：
Asymmetric Catalysis; Bispyrrolidine Diboronates; Diels-Alder Reaction; Exo-Selectivity; Pericyclic Reaction; ASYMMETRIC TOTAL-SYNTHESIS; CYCLOADDITION REACTIONS; CHIRAL CATALYSTS; EXO-SELECTIVITY; DESIGN; ACIDS; DIENOPHILES;
D O I：
10.1002/anie.202303075
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly enantioselective catalytic system for exo-Diels-Alder reactions was developed based on the newly discovered bispyrrolidine diboronates (BPDB). Activated by various Lewis or Bronsted acids, BPDB can catalyze highly stereoselective asymmetric exo-Diels-Alder reactions of monocarbonyl-based dienophiles. When 1,2-dicarbonyl-based dienophiles are used, the catalyst can sterically distinguish between the two binding sites, which leads to highly regioselective asymmetric Diels-Alder reactions. BPDB can be prepared as crystalline solids on a large scale and are stable under ambient condition. Single-crystal X-ray analysis of the structure for acid-activated BPDB indicated that its activation involves cleavage of a labile B & LARR;N bond.
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页数：7
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