Enantioselective N-Heterocyclic Carbene-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Oxidation

被引：206

作者：

Rong, Zi-Qiang ^{[1
]}

Jia, Min-Qiang ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 15期

基金：

中国国家自然科学基金;

关键词：

INTRAMOLECULAR STETTER REACTION; SPIRO-GAMMA-BUTYROLACTONES; KETONE BENZOIN REACTIONS; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC CARBENES; AROMATIC-ALDEHYDES; EFFICIENT SYNTHESIS; DIRECT ANNULATIONS; TRIAZOLIUM SALTS; RING EXPANSION;

D O I：

10.1021/ol201595f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective N-heterocyclic carbene-catalyzed Michael addition reactions to alpha,beta-unsaturated aldehydes by redox oxidation were realized. With 10 mol % of camphor-derived triazolium salt D, 15 mol % of DBU, 5 mol % of NaBF4, and 100 mol % of quinone oxidant, the reactions of various dicarbonyl compounds with alpha,beta-unsaturated aldehydes led to 3,4-dihydro-alpha-pyrones in good yields and excellent ee's.

引用

页码：4080 / 4083

页数：4

共 119 条

[1]

ALANIZ JR, 2008, J ORG CHEM, V130, P2033

[2] Intermolecular N-Heterocyclic Carbene Catalyzed Hydroacylation of Arynes [J].

Biju, Akkattu T. ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) :9761-9764

[3] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes [J].

Biju, Akkattu T. ;

Wurz, Nathalie E. ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5970-+

[4] N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].

Bode, Jeffrey W. ;

Sohn, Stephanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+

[5] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[6] The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters [J].

Candish, Lisa ;

Lupton, David W. .

ORGANIC LETTERS, 2010, 12 (21) :4836-4839

[7] Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates [J].

Cardinal-David, Benoit ;

Raup, Dustin E. A. ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5345-+

[8] Direct amination of homoenolates catalyzed by N-Heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2740-+

[9] Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions [J].

Chiang, Pei-Chen ;

Kaeobamrung, Juthanat ;

Bode, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3520-+

[10] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].

Chow, KYK ;

Bode, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127

← 1 2 3 4 5 6 7 8 9 10 →