Enantioselective Synthesis of Dihydrocoumarins via N-Heterocyclic Carbene-Catalyzed Cycloaddition of Ketenes and o-Quinone Methides

被引：148

作者：

Lv, Hui ^{[1
]}

You, Lin ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cycloadditions; dihydrocoumarins; ketenes; N-heterocyclic carbenes; BAYLIS-HILLMAN REACTION; NUCLEOPHILIC CARBENES; GAMMA-BUTYROLACTONES; ACID; 3,4-DIHYDROCOUMARINS; DERIVATIVES; COUMARINS; ALDEHYDES; ORGANOCATALYSIS; HYDROARYLATION;

D O I：

10.1002/adsc.200900544

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [4+2] cycloaddition reaction of alky(aryl)ketenes and o-quinone methides to give the corresponding 3,3,4-trisubstituted 3,4-dihydrocoumarins in good yields with good diastereoselectivities and excellent enantioselectivities.

引用

页码：2822 / 2826

页数：5

共 48 条

[1] Asymmetric Cycloadditions of o-Quinone Methides Employing Chiral Ammonium Fluoride Precatalysts [J].

Alden-Danforth, Ethan ;

Scerba, Michael T. ;

Lectka, Thomas .

ORGANIC LETTERS, 2008, 10 (21) :4951-4953

[2]

[Anonymous], 2009, ANGEW CHEM

[3]

[Anonymous], 2004, ANGEW CHEM

[4] A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives [J].

Aoki, S ;

Amamoto, C ;

Oyamada, J ;

Kitamura, T .

TETRAHEDRON, 2005, 61 (39) :9291-9297

[5] Unprecedented reactivity pattern of chromium Fischer carbene complexes. Direct application to one-pot synthesis of 4-aryl-3,4-dihydrocoumarins on a multigram scale [J].

Barluenga, Jose ;

Andina, Facundo ;

Aznar, Fernando .

ORGANIC LETTERS, 2006, 8 (13) :2703-2706

[6] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[7]

BRESLOW R, 1958, J AM CHEM SOC, V80, P3119

[8] 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

[9] Heterocycles derived from heteroatom-substituted carbenes [J].

Cheng, Y ;

Meth-Cohn, O .

CHEMICAL REVIEWS, 2004, 104 (05) :2507-2530

[10] Substrate-controlled and site-selective [3+2] cycloadditions of N-heterocyclic carbene derived ambident dipoles [J].

Cheng, Ying ;

Liu, Mei-Fang ;

Fang, De-Cai ;

Lei, Xue-Mei .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (15) :4282-4292

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