Asymmetric Organocatalytic Domino Michael/Aldol Reactions: Enantioselective Synthesis of Chiral Cycloheptanones, Tetrahydrochromenones, and Polyfunctionalized Bicyclo-[3.2.1]octanes

被引:139
作者
Rueping, Magnus [1 ]
Kuenkel, Alexander [1 ]
Tato, Francisco [1 ]
Bats, Jan W. [2 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[2] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-6000 Frankfurt, Germany
关键词
aldol reaction; domino reaction; Michael addition; organocatalysis; prolinol ethers; RETRO-ALDOL REACTION; BRONSTED ACID; ALPHA; BETA-UNSATURATED ALDEHYDES; CATALYZED REACTION; TRANSFER HYDROGENATION; CASCADE; TANDEM; STEREOCENTERS; 1,2-DIKETONES; CONSTRUCTION;
D O I
10.1002/anie.200900754
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C! mon 1,2-dione: A new diastereo- and enantioselective Lewis base catalyzed domino Michael/aldol reaction converts α, β-unsaturated aldehydes and 1,2-diones into chiral bicyclo[3.2.1]octane-6- carbaldehydes. The products are produced in good to excellent enantioselectivities (90- 98 % ee) and can be transformed into bicyclic diols and triols. Additionally, a retroaldol cyclization provides access to valuable tetrahydrochromenones (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3699 / 3702
页数:4
相关论文
共 100 条
[1]   RETRO-ALDOL REACTION OF RETINYLIDENE-1,3-DIKETONES - CORRELATION WITH BIOLOGICAL-ACTIVITY [J].
ACTON, N ;
BROSSI, A .
HELVETICA CHIMICA ACTA, 1980, 63 (06) :1396-1399
[2]  
[Anonymous], 2007, ANGEW CHEM-GER EDIT
[3]  
[Anonymous], 2008, ANGEW CHEM
[4]   Controlling the formation of 1 out of 64 stereoisomers using organocatalysis [J].
Bertelsen, Soren ;
Johansen, Rasmus L. ;
Jorgensen, Karl Anker .
CHEMICAL COMMUNICATIONS, 2008, (26) :3016-3018
[5]   Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].
Brandau, Sven ;
Maerten, Eddy ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14986-14991
[6]   A proline-catalyzed asymmetric Robinson annulation reaction [J].
Bui, T ;
Barbas, CF .
TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954
[7]   Tandem and domino catalytic strategies for enantioselective synthesis [J].
Chapman, Christopher J. ;
Frost, Christopher G. .
SYNTHESIS-STUTTGART, 2007, (01) :1-21
[8]   3-Formylcyclopent-3-enyl- and 3-carboxycyclopentylglycine derivatives: A new stereocontrolled approach via retro-aldol or retro-Claisen reactions [J].
Clerici, F ;
Gelmi, ML ;
Pellegrino, S ;
Pilati, T .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5286-+
[9]   Indolocarbazoles: a new family of anion sensors [J].
Curiel, D ;
Cowley, A ;
Beer, PD .
CHEMICAL COMMUNICATIONS, 2005, (02) :236-238
[10]   Parallel synthesis of pteridine derivatives as potent inhibitors for hepatitis C virus NS5B RNA-dependent RNA polymerase [J].
Ding, Y ;
Girardet, JL ;
Smith, KL ;
Larson, G ;
Prigaro, B ;
Lai, VCH ;
Zhong, WD ;
Wu, JZ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :675-678