Asymmetric chemo- and regiospecific addition of organozinc reagents to Baylis-Hillman derived allylic electrophiles

被引:48
作者
Börner, C
Gimeno, J
Gladiali, S
Goldsmith, PJ
Ramazzotti, D
Woodward, S
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain
[3] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1039/b006943o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalysed S(N)2' addition of ZnR2 to allylic (Z)-ArCH=C(CH2X)(CO2Et) (X = Br, Cl, OSO2Me) fashions only ArCH(R)C(=CH2)(CO2Et); use of a chiral ligand gives up to 64% ee for this demanding reaction.
引用
收藏
页码:2433 / 2434
页数:2
相关论文
共 19 条
[1]   Diphenylpropionic acids as new AT(1) selective angiotensin II antagonists [J].
Almansa, C ;
Gomez, LA ;
Cavalcanti, FL ;
deArriba, AF ;
Rodriguez, R ;
Carceller, E ;
GarciaRafanell, J ;
Forn, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) :2197-2206
[2]   NECIC ACID SYNTHONS .2. REGIOSELECTIVITY IN THE REACTIONS OF (Z)-2-BROMOMETHYL-2-ALKENOATE ESTERS WITH SELECTED CARBON NUCLEOPHILES [J].
AMEER, F ;
DREWES, SE ;
EMSLIE, ND ;
KAYE, PT ;
MANN, RL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2293-2295
[3]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[4]   Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones [J].
Bennett, SMW ;
Brown, SM ;
Cunningham, A ;
Dennis, MR ;
Muxworthy, JP ;
Oakley, MA ;
Woodward, S .
TETRAHEDRON, 2000, 56 (18) :2847-2855
[5]  
Dübner F, 1999, ANGEW CHEM INT EDIT, V38, P379, DOI 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO
[6]  
2-Y
[7]  
DUBNER F, 2000, CHEM ABST 222063, V132
[8]   Regio- and enantio-selective allylic alkylation catalysed by a chiral monophosphine-palladium complex [J].
Hayashi, T ;
Kawatsura, M ;
Uozumi, Y .
CHEMICAL COMMUNICATIONS, 1997, (06) :561-562
[9]   First enantioselective alkylations of monosubstituted allylic acetates catalyzed by chiral iridium complexes [J].
Janssen, JP ;
Helmchen, G .
TETRAHEDRON LETTERS, 1997, 38 (46) :8025-8026
[10]   TETRAKIS(ACETONITRILE)COPPER(1+) HEXAFLUOROPHOSPHATE(1-) - CU2O+2HPF6CH3CN-]2[CU(CH3CN)4][PF6]+H2O [J].
KUBAS, GJ .
INORGANIC SYNTHESES, 1990, 28 :68-70