Enantioselective [3+2] Annulation of Enals with 2-Aminoacrylates Catalyzed by N-Heterocyclic Carbene

被引：22

作者：

Li, Xing-Shuo ^{[1
]}

Zhao, Liang-Liang ^{[1
]}

Wang, Xiao-Ke ^{[1
]}

Cao, Li-Li ^{[1
]}

Shi, Xiao-Qian ^{[1
]}

Zhang, Rui ^{[1
]}

Qi, Jing ^{[1
,2
]}

机构：

[1] Hebei Univ, Coll Chem & Environm Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Peoples R China

[2] Hebei Univ, Minist Educ, Key Lab Med Chem & Mol Diag, Baoding 071002, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

中国国家自然科学基金;

关键词：

GAMMA-LACTAM OXINDOLES; COOPERATIVE CATALYSIS; HOMOENOLATE ADDITIONS; ASYMMETRIC-SYNTHESIS; NHC CATALYSIS; ACTIVATION; ORGANOCATALYSIS; ALDEHYDES; KETIMINES; ELECTROPHILES;

D O I：

10.1021/acs.orglett.7b01860

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and convenient strategy for the enantioselective synthesis of gamma-lactam derivatives via N-heterocyclic carbene catalyzed formal [3 + 2] annulation of enals with 2-aminoacrylates is disclosed. This activation mode provides a complementary approach to the synthesis of various gamma-lactam derivatives in good yields with excellent diastereo- and enantioselectivities. In this process, two consecutive stereocenters are constructed, and a quaternary carbon center is also established.

引用

页码：3943 / 3946

页数：4

共 48 条

[1] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(1,2-DIHYDRO-2-OXO-1-PYRIDYL)-2H-1-BENZOPYRANS AND RELATED-COMPOUNDS, NEW POTASSIUM CHANNEL ACTIVATORS [J].

BERGMANN, R ;

GERICKE, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :492-504

[2] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[3] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[4] Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes [J].

Chen, Xiang-Yu ;

Ye, Song .

SYNLETT, 2013, 24 (13) :1614-1622

[5] Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent [J].

Collett, Christopher J. ;

Massey, Richard S. ;

Maguire, Oliver R. ;

Batsanov, Andrei S. ;

O'Donoghue, AnnMarie C. ;

Smith, Andrew D. .

CHEMICAL SCIENCE, 2013, 4 (04) :1514-1522

[6] Catalysis with N-Heterocyclic Carbenes under Oxidative Conditions [J].

De Sarkar, Suman ;

Biswas, Anup ;

Samanta, Ramesh C. ;

Studer, Armido .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (15) :4664-4678

[7] Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction [J].

Di Maso, Michael J. ;

Nepomuceno, Gabriella M. ;

St Peter, Michael A. ;

Gitre, Haley H. ;

Martin, Kevin S. ;

Shaw, Jared T. .

ORGANIC LETTERS, 2016, 18 (08) :1740-1743

[8] Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst [J].

DiRocco, Daniel A. ;

Noey, Elizabeth L. ;

Houk, K. N. ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) :2391-2394

[9] NHCs in Asymmetric Organocatalysis: Recent Advances in Azolium Enolate Generation and Reactivity [J].

Douglas, James ;

Churchill, Gwydion ;

Smith, Andrew D. .

SYNTHESIS-STUTTGART, 2012, 44 (15) :2295-2309

[10] Discovery of γ-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor α converting enzyme:: Design, synthesis, and structure-activity relationships [J].

Duan, JJW ;

Chen, LH ;

Wasserman, ZR ;

Lu, ZH ;

Liu, RQ ;

Covington, MB ;

Qian, MX ;

Hardman, KD ;

Magolda, RL ;

Newton, RC ;

Christ, DD ;

Wexler, RR ;

Decicco, CP .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (23) :4954-4957

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