Oxidative Asymmetric [2+3] Annulation of Aldehydes with Azomethine Imines Enabled by N-Heterocyclic Carbene Catalysis

被引：48

作者：

Yuan, Shim ^{[1
]}

Luo, Yuchen ^{[1
]}

Peng, Jingyi ^{[1
]}

Miao, Maozhong ^{[1
]}

Xu, Jianfeng ^{[1
]}

Ren, Hongjun ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ISATIN-DERIVED KETIMINES; ALPHA-CHLOROALDEHYDES; PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; SOMO ACTIVATION; ORGANOCATALYSIS; ACCESS; ACID;

D O I：

10.1021/acs.orglett.7b02948

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric [2 + 3] annulation of simple aldehydes with N,N'-cyclic azomethine imines via oxidative N-heterocyclic carbene (NHC) catalysis is disclosed, affording bicyclic pyrazolidinones bearing two vicinal tertiary stereogenic centers with moderate to good yields (56-84% for 19 examples), good to excellent diastereoselectivities (>20:1 for 17 examples), and good to excellent enantioselectivities (66-98% for 19 examples). This direct alpha-carbon functionalization reaction of aldehyde can be readily performed on gram scale under mild conditions, and a five-membered transition state is proposed to rationalize the stereochemical outcome.

引用

页码：6100 / 6103

页数：4

共 64 条

[1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[2] Development of a tailor-made bis(oxazolidine)pyridine-metal catalyst for the [3+2] cycloaddition of azomethine imines with propiolates [J].

Arai, Takayoshi ;

Ogino, Yuta ;

Sato, Toru .

CHEMICAL COMMUNICATIONS, 2013, 49 (71) :7776-7778

[3] Enantioselective organocatalysis using SOMO activation [J].

Beeson, Teresa D. ;

Mastracchio, Anthony ;

Hong, Jun-Bae ;

Ashton, Kate ;

MacMillan, David W. C. .

SCIENCE, 2007, 316 (5824) :582-585

[4] Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5334-+

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

Chen, Xiang-Yu ;

Ye, Song .

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

[6] Cooperative Lewis acid/N-heterocyclic carbene catalysis [J].

Cohen, Daniel T. ;

Scheidt, Karl A. .

CHEMICAL SCIENCE, 2012, 3 (01) :53-57

[7] Diaminocyclopropenylidene Organocatalysts: Beyond N-Heterocyclic Carbenes [J].

Connon, Stephen J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) :1203-1205

[8] 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

[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] Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral [J].

Douglas, James J. ;

Churchill, Gwydion ;

Slawin, Alexandra M. Z. ;

Fox, David J. ;

Smith, Andrew D. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) :16354-16358

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