Asymmetric 1,3-Dipolar Cycloaddition Reactions of Enones by Primary Amine Catalysis

被引：5

作者：

Yang, Qi ^{[1
,2
]}

Zhang, Jieyu ^{[1
,2
]}

Jia, Zongbin ^{[1
,2
]}

Yang, Chunming ^{[3
]}

Zhang, Long ^{[1
,2
,3
]}

Luo, Sanzhong ^{[1
,2
,3
]}

机构：

[1] Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100490, Peoples R China

[3] Tsinghua Univ, Ctr Basic Mol Sci, Dept Chem, Beijing 100084, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 07期

关键词：

1; 3-dipolar cycloaddition; primary amine catalysis; iminium intermediate; isoxazolidine derivatives; BETA-KETOCARBONYLS; ONE-POT; NITRONES; ISOXAZOLIDINE; KETONES; DESIGN; REMOTE;

D O I：

10.1002/ajoc.201900013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a 1,3-dipolar cycloaddition between enones and nitrones with good to excellent distereo- and enantioselectivities by a chiral primary amine catalyst, which furnishes an operationally simple synthetic protocol for the fused bicyclic isoxazolidine derivatives with multiple stereogenic centers.

引用

页码：1049 / 1052

页数：4

共 44 条

[1] Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition:: a concise asymmetric total synthesis of (-)-rosmarinecine [J].

Akai, S ;

Tanimoto, K ;

Kanao, Y ;

Omura, S ;

Kita, Y .

CHEMICAL COMMUNICATIONS, 2005, (18) :2369-2371

[2] Total synthesis of pyridovericin: Studies toward the biomimetic synthesis of pyridomacrolidin [J].

Baldwin, JE ;

Adlington, RM ;

Conte, A ;

Irlapati, NR ;

Marquez, R ;

Pritchard, GJ .

ORGANIC LETTERS, 2002, 4 (13) :2125-2127

[3] Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry [J].

Berthet, Matheo ;

Cheviett, Thomas ;

Dujardin, Gilles ;

Parrot, Isabelle ;

Martinez, Jean .

CHEMICAL REVIEWS, 2016, 116 (24) :15235-15283

[4]

CesardaSilva R., 2014, ASIAN J ORG CHEM, V3, P466

[5] Regioselective Asymmetric Formal (3+2) Cycloadditions of Nitrone Ylides from Isatins and Enals [J].

Chen, Yu-Rong ;

Zhan, Gu ;

Du, Wei ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) :3759-3764

[6] A new organocatalyst for 1,3-dipolar cycloadditions of nitrones to α,β-unsaturated aldehydes [J].

Chow, San San ;

Nevalainen, Marta ;

Evans, Catherine A. ;

Johannes, Charles W. .

TETRAHEDRON LETTERS, 2007, 48 (02) :277-280

[7] Beyond Classical Reactivity Patterns: Shifting from 1,4-to 1,6-Additions in Regio- and Enantioselective Organocatalyzed Vinylogous Reactions of Olefinic Lactones with Enals and 2,4-Dienals [J].

Dell'Amico, Luca ;

Albrecht, Lukasz ;

Naicker, Tricia ;

Poulsen, Pernille H. ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) :8063-8070

[8] Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].

Frederickson, M .

TETRAHEDRON, 1997, 53 (02) :403-425

[9] Chiral Primary-Amine-Catalyzed Conjugate Addition to α-Substituted Vinyl Ketones/Aldehydes: Divergent Stereocontrol Modes on Enamine Protonation [J].

Fu, Niankai ;

Zhang, Long ;

Luo, Sanzhong ;

Cheng, Jin-Pei .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (46) :15669-15681

[10] Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate [J].

Fu, Niankai ;

Zhang, Long ;

Li, Jiuyuan ;

Luo, Sanzhong ;

Cheng, Jin-Pei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) :11451-11455

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