Asymmetric Synthesis of Spiro-3,4-dihydropyrans via a Domino Organocatalytic Sequence

被引：56
作者：
Yao, Weijun [1 ]
Pan, Lianjie [1 ]
Wu, Yihua [1 ]
Ma, Cheng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 10期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTIONS; CATALYTIC ENANTIOSELECTIVE CONSTRUCTION; CARBON QUATERNARY STEREOCENTERS; MICHAEL-ALDOL REACTIONS; CONJUGATE ADDITION; NONADJACENT STEREOCENTERS; CINCHONA ALKALOIDS; NATURAL-PRODUCTS; DERIVATIVES; ACTIVATION;
D O I：
10.1021/ol1007873
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cinchona alkaloid-catalyzed domino Michael/hemiacetalization reaction of cyclic beta-oxo aldehydes and aromatic beta,gamma-unsaturated a-keto esters, resulting in the formation of spiro-dihydropyran architectures in good yield with high stereoselectivity (up to 97% ee), is presented.
引用
收藏
页码：2422 / 2425
页数：4
相关论文
共 59 条
[1]   Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].
Aho, JE ;
Pihko, PM ;
Rissa, TK .
CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440
[2]   Organocatalytic Domino Reactions [J].
Alba, Andrea-Nekane ;
Companyo, Xavier ;
Viciano, Monica ;
Rios, Ramon .
CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) :1432-1474
[3]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[4]   Catalytic, Asymmetric Michael Reactions of Cyclic Diketones with β,γ-Unsaturated α-Ketoesters [J].
Calter, Michael A. ;
Wang, Jun .
ORGANIC LETTERS, 2009, 11 (10) :2205-2208
[5]   Asymmetric alcoholysis of cyclic anhydrides [J].
Chen, YG ;
McDaid, P ;
Deng, L .
CHEMICAL REVIEWS, 2003, 103 (08) :2965-2983
[6]   Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].
Connon, Stephen J. .
CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510
[7]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[8]  
2-V
[9]   Enantioselective catalytic formation of quaternary stereogenic centers [J].
Cozzi, Pier Giorgio ;
Hilgraf, Robert ;
Zimmermann, Nicole .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :5969-5994
[10]   Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones [J].
Dickmeiss, Gustav ;
De Sio, Vincenzo ;
Udmark, Jonas ;
Poulsen, Thomas B. ;
Marcos, Vanesa ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6650-6653
123456