N-Heterocyclic Carbene (NHC)-Catalyzed Highly Diastereo- and Enantioselective Oxo-Diels-Alder Reactions for Synthesis of Fused Pyrano[2,3-b]indoles

被引：97

作者：

Yang, Limin ^{[1
,2
,3
]}

Wang, Fei ^{[1
,2
,3
]}

Chua, Pei Juan ^{[3
]}

Lv, Yunbo ^{[3
]}

Zhong, Liang-Jun ^{[1
,2
]}

Zhong, Guofu ^{[1
,2
]}

机构：

[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

[2] Hangzhou Normal Univ, Sch Med, Hangzhou 310036, Zhejiang, Peoples R China

[3] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

关键词：

STABLE CARBENES; DERIVATIVES; STEREOCHEMISTRY; CYCLIZATION; CATALYSIS; ALDEHYDES;

D O I：

10.1021/ol301175z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and alpha-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).

引用

页码：2894 / 2897

页数：4

共 49 条

[1]

[Anonymous], TETRAHEDRON

[2] SYNTHESIS AND STEREOCHEMISTRY OF SOME ISATYLIDENEACETIC ACID DERIVATIVES [J].

AUTREY, RL ;

TAHK, FC .

TETRAHEDRON, 1967, 23 (02) :901-&

[3] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

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

[4] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[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] 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-+

[7]

Chiang P.-C., 2011, TCI MAIL, V149, P2

[8] Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one [J].

Das, Biswanath ;

Laxminarayana, Keetha ;

Krishnaiah, Martha ;

Kumar, Duddukuri Nandan .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (22) :6396-6398

[9]

Dewick P. M., 2002, MED NATURAL PRODUCTS

[10] The first asymmetric intramolecular Stetter reaction [J].

Enders, D ;

Breuer, K ;

Runsink, J ;

Teles, JH .

HELVETICA CHIMICA ACTA, 1996, 79 (07) :1899-1902

← 1 2 3 4 5 →