Regio- and enantioselective iridium-catalyzed allylic alkylation with in situ activated P,C-chelate complexes

被引:133
作者
Lipowsky, G [1 ]
Miller, N [1 ]
Helmchen, G [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
alkylation; allylic substitution; asymmetric catalysis; iridium; phosphorus amidites;
D O I
10.1002/anie.200460016
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Come together: Successful cooperation of iridium and copper yielded a new catalyst system for allylic alkylation. Branched alkylation products can be obtained rapidly and with high enantioselectivity from simple linear precursors (see scheme; cod = cyclooctadiene).
引用
收藏
页码:4595 / 4597
页数:3
相关论文
共 21 条
[1]  
[Anonymous], ANGEW CHEM
[2]  
Bartels B, 2003, EUR J ORG CHEM, V2003, P1097
[3]  
Bartels B, 2002, EUR J INORG CHEM, P2569
[4]   Ir-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands [J].
Bartels, B ;
Helmchen, G .
CHEMICAL COMMUNICATIONS, 1999, (08) :741-742
[5]   Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353
[6]   Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): Catalytic, kinetic resolution of allyl carbonates [J].
Fischer, C ;
Defieber, C ;
Suzuki, T ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1628-1629
[7]   Enantioselective molybdenum-catalyzed allylic alkylation using chiral bisoxazoline ligands [J].
Glorius, F ;
Pfaltz, A .
ORGANIC LETTERS, 1999, 1 (01) :141-144
[8]   First enantioselective alkylations of monosubstituted allylic acetates catalyzed by chiral iridium complexes [J].
Janssen, JP ;
Helmchen, G .
TETRAHEDRON LETTERS, 1997, 38 (46) :8025-8026
[9]   Identification of an activated catalyst in the iridium-catalyzed allylic amination and etherification. Increased rates, scope, and selectivity [J].
Kiener, CA ;
Shu, CT ;
Incarvito, C ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14272-14273
[10]   Regio- and enantioselective iridium-catalysed allylic aminations and alkylations of dienyl esters [J].
Lipowsky, G ;
Helmchen, G .
CHEMICAL COMMUNICATIONS, 2004, (01) :116-117