Synthesis of aminophosphine ligands with binaphthyl backbones for silver (I)-catalyzed enantioselective allylation of benzaldehyde

被引:0
作者
Wang, Y [1 ]
Ji, BM [1 ]
Ding, KL [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
silver; aminophosphine ligand; asymmetric catalysis; allylation;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of aminophosphine ligands was synthesized from 2-amino-2'-hydroxy-1,1'-binaphthyI (NOBIN). Their asymmetric induction efficiency was examined for silver(I) catalyzed enantioselective allylation reaction of benzaldehyde with allyl-tributyltin. Under the optimized reaction conditions, quantitative yield as well as moderate ee value (54.5% ee) of product was achieved by the catalysis with silver(l)/3 complex. The effects of the binaplithyl backbone and the substitutes situated at chelating N, P atoms on enantioselectivity of the reaction were also discussed.
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页码:1300 / 1312
页数:13
相关论文
共 36 条
[1]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].
AOKI, S ;
MIKAMI, K ;
TERADA, M ;
NAKAI, T .
TETRAHEDRON, 1993, 49 (09) :1783-1792
[2]   ENANTIOSELECTIVE SYNTHESIS OF HOMO-ALLYLIC ALCOHOLS FROM CHIRAL ALLYLIC TIN(IV) (+)-DIETHYL TARTRATE COMPLEXES AND ALDEHYDES [J].
BOLDRINI, GP ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (09) :685-686
[4]   A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].
COREY, EJ ;
YU, CM ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5495-5496
[5]   CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].
COSTA, AL ;
PIAZZA, MG ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002
[6]  
Ding KL, 1999, CHEM-EUR J, V5, P1734, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1734::AID-CHEM1734>3.3.CO
[7]  
2-7
[8]   Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine [J].
Ding, KL ;
Xu, QG ;
Wang, Y ;
Liu, JX ;
Yu, ZY ;
Du, BS ;
Wu, YJ ;
Koshima, H ;
Matsuura, T .
CHEMICAL COMMUNICATIONS, 1997, (07) :693-694
[9]  
GRAYSON M, 1967, TETRAHEDRON, P1065
[10]  
Guo H, 2001, CHINESE J CHEM, V19, P52