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.

引用

页数：7

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