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

共 56 条

[31] Asymmetric Total Synthesis of Lancifodilactone G Acetate [J].

Liu, Dong-Dong ;

Sun, Tian-Wen ;

Wang, Kuang-Yu ;

Lu, Yong ;

Zhang, Su-Lei ;

Li, Yuan-He ;

Jiang, Yan-Long ;

Chen, Jia-Hua ;

Yang, Zhen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (16) :5732-5735

[32] Chiral oxazaborolidine-aluminum bromide complexes are unusually powerful and effective catalysts for enantioselective Diels-Alder reactions [J].

Liu, Duan ;

Canales, Eda ;

Corey, E. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1498-+

[33] Multicatalytic Asymmetric Synthesis of Complex Tetrahydrocarbazoles via a Diels-Alder/Benzoin Reaction Sequence [J].

Liu, Yankai ;

Nappi, Manuel ;

Escudero-Adan, Eduardo C. ;

Melchiorre, Paolo .

ORGANIC LETTERS, 2012, 14 (05) :1310-1313

[34] Unique Steric Effect of Geminal Bis(silane) To Control the High Exo-selectivity in Intermolecular Diels-Alder Reaction [J].

Liu, Zengjin ;

Lin, Xinglong ;

Yang, Na ;

Su, Zhishan ;

Hu, Changwei ;

Xiao, Peihong ;

He, Yanyang ;

Song, Zhenlei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) :1877-1883

[35] Enzyme catalysed kinetic resolution of racemic methyl 3-acethylbicyclo [2.2.1] hept-5-ene-2-carboxylate using pig's liver esterase [J].

Mamaghani, M ;

Alizadehnia, A .

JOURNAL OF CHEMICAL RESEARCH, 2002, (08) :386-387

[36] DISCRIMINATION OF 2 DIFFERENT ESTER CARBONYLS WITH METHYLALUMINUM BIS(2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE) - APPLICATION TO THE REGIOCONTROLLED AND STEREOCONTROLLED DIELS-ALDER REACTION OF UNSYMMETRICAL FUMARATES [J].

MARUOKA, K ;

SAITO, S ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :1089-1090

[37] CATALYTIC ASYMMETRIC GLYOXYLATE ENE REACTION - A PRACTICAL ACCESS TO ALPHA-HYDROXY ESTERS IN HIGH ENANTIOMERIC PURITIES [J].

MIKAMI, K ;

TERADA, M ;

NAKAI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :3949-3954

[38]

Miklós F, 2002, HETEROCYCLES, V57, P2309

[39] Diels-Alder Reactions of β-Acylacrylic Acids [J].

Miles, William H. ;

Cohen, Evan M. ;

Naimoli, Barbara J. .

SYNTHETIC COMMUNICATIONS, 2013, 43 (14) :1980-1991

[40] Recent advances of Diels-Alderases involved in natural product biosynthesis [J].

Minami, Atsushi ;

Oikawa, Hideaki .

JOURNAL OF ANTIBIOTICS, 2016, 69 (07) :500-506

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