Chiral counteranions in asymmetric transition-metal catalysis:: Highly enantioselective Pd/Bronsted acid-catalyzed direct α-allylation of aldehydes

被引:520
作者
Mukherjee, Santanu [1 ]
List, Benjamin [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/ja074678r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have developed a highly enantioselective Pd/chiral acid-catalyzed alpha-allylation of alpha-branched aldehydes with an allyl amine as the allylating species that creates all-carbon quaternary stereogenic centers in high yields and enantioselectivities. To our knowledge, this is the first time that a chiral anionic ligand is applied for achieving asymmetric induction in a palladium-catalyzed allylic alkylation reaction.
引用
收藏
页码:11336 / +
页数:3
相关论文
共 40 条
[1]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[2]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[3]   ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE [J].
ALPER, H ;
HAMEL, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2803-2804
[4]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[5]   Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers [J].
Belanger, Etienne ;
Cantin, Katy ;
Messe, Olivier ;
Tremblay, Melanie ;
Paquin, Jean-Francois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1034-1035
[6]  
BENENNA DC, 2004, J AM CHEM SOC, V126, P15044
[7]   New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates [J].
Braun, M ;
Meier, T .
SYNLETT, 2006, (05) :661-676
[8]   Tsuji-Trost allylic alkylation with ketone enolates [J].
Braun, Manfred ;
Meier, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :6952-6955
[9]   Stereoselective construction of quaternary stereocenters [J].
Christoffers, J ;
Baro, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482
[10]   Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912