Tandem Metal and Organocatalysis in Sequential Hydroformylation and Enantioselective Mannich Reactions

被引:53
作者
Chercheja, Serghei [1 ]
Rothenbuecher, Thomas [1 ]
Eilbracht, Peter [1 ]
机构
[1] Tech Univ Dortmund, Fachbereich Chem, D-44227 Dortmund, Germany
关键词
hydroformylation; Mannich reaction; organocatalysis; tandem reactions; TETRAHYDRO-BETA-CARBOLINES; ONE-POT; TRANSITION-METAL; CATALYSIS; ACID; 3-COMPONENT; COMBINATION; ALDEHYDES; ALCOHOLS; ENAMINE;
D O I
10.1002/adsc.200800720
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Metal-catalysed hydroformylation is successfully combined with an organocatalysed stereoselective Mannich reaction in a tandem reaction sequence. This novel type of "tandem catalysis" allows access to complex molecular systems with high levels of enantioselectivity, using simple starting materials and an amino acid as the chiral catalyst.
引用
收藏
页码:339 / 344
页数:6
相关论文
共 42 条
[1]   Domino hydroformylation/enantioselective cross-aldol addition [J].
Abillard, Olivier ;
Breit, Bernhard .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1891-1895
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], TRANSITION METALS OR
[4]   Combining two-directional synthesis and tandem reactions. Part 4: A concise approach to the spirocyclic core of halichlorine and the pinnaic acids [J].
Arini, LG ;
Szeto, P ;
Hughes, DL ;
Stockman, RA .
TETRAHEDRON LETTERS, 2004, 45 (45) :8371-8374
[5]   A novel access to tetrahydro-β-carbolines via one-pot hydroformylation/Fischer indlole synthesis:: Rearrangement of 3,3-spiroindoleninium cations [J].
Bondzic, Bojan P. ;
Eilbracht, Peter .
ORGANIC LETTERS, 2008, 10 (16) :3433-3436
[6]   Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation-Fischer indole synthesis [J].
Bondzic, Bojan P. ;
Farwick, Andreas ;
Liebich, Jens ;
Eilbracht, Peter .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (20) :3723-3731
[7]   Syntheses of tetrahydro-β-carbolines via a tandem hydroformylation-Pictet- Spengler reaction. Scope and limitations [J].
Bondzic, Bojan P. ;
Eilbracht, Peter .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (21) :4059-4063
[8]   Domino hydroformylation-Wittig olefination-hydrogenation [J].
Breit, B ;
Zahn, SK .
TETRAHEDRON, 2005, 61 (26) :6171-6179
[9]  
Breit B, 2001, SYNTHESIS-STUTTGART, P1
[10]  
Breit B, 2001, ANGEW CHEM INT EDIT, V40, P1910, DOI 10.1002/1521-3773(20010518)40:10<1910::AID-ANIE1910>3.3.CO