The catalytic asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines catalyzed by Cu(OTf)2-chiral N-(binaphthyl-2-yl)thiophosphoramide ligands

被引：39

作者：

Shi, M ^{[1
]}

Wang, CJ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2003年 / 345卷 / 08期

关键词：

N-(arylmethylene)-P; P-diphenylphosphinic amides; asymmetric addition; asymmetric catalysis; chiral N-(thiophosphoryl)-1,1 '-binaphthyl-2 ',2-diamine; copper(II) triflate; diethylzinc; imines; N ligands;

D O I：

10.1002/adsc.200303041

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral N-(binaphthyl-2-yl)thiophosphoramide L7 [O,O-diethyl 2'-(ethylamino)-1,1'-binaphthyl-2-viamidothiophosphate] prepared from the reaction of diethyl chlorothiophosphate with (R)-(+)-N-ethyl- 1,1'-binaphthyl-2,2'-diamine was used as a catalytic chiral ligand in the first Cu(OTf)(2)-promoted catalytic asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines in which similar to85% ee can be realized.

引用

页码：971 / 973

页数：3

共 29 条

[1] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].

Andersson, PG ;

Guijarro, D ;

Tanner, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375

[2] Preparation and application of a polymer-supported chiral π-allylpalladium catalyst for the allylation of imines [J].

Bao, M ;

Nakamura, H ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 2000, 41 (01) :131-134

[3] Enantioselective addition of diethylzinc to a N-diphenylphosphinoylimine employing cinchona alkaloids as chiral ligands [J].

Beresford, KJM .

TETRAHEDRON LETTERS, 2002, 43 (40) :7175-7177

[4] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines [J].

Boezio, AA ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1692-1693

[5]

Brandt P, 1999, CHEM-EUR J, V5, P1692, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO

[6]

2-M

[7] CRYSTAL AND MOLECULAR-STRUCTURES OF (1,8-BIS(2-PYRIDYL)-3,6-DITHIAOCTANE)COPPER(I) HEXAFLUOROPHOSPHATE AND PERCHLORATO(1,8-BIS(2-PYRIDYL)-3,6-DITHIAOCTANE)COPPER(II) PERCHLORATE - STEREODYNAMICS OF THE COPPER(II)-COPPER(I) COUPLE [J].

BRUBAKER, GR ;

BROWN, JN ;

YOO, MK ;

KINSEY, RA ;

KUTCHAN, TM ;

MOTTEL, EA .

INORGANIC CHEMISTRY, 1979, 18 (02) :299-302

[8] ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].

DENMARK, SE ;

NAKAJIMA, N ;

NICAISE, OJC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798

[9] Effect of ligand structure in the bisoxazoline mediated asymmetric addition of methyllithium to imines [J].

Denmark, SE ;

Stiff, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5875-5878

[10]

Federsel H.-J., 1997, CHIRALITY IND, P225

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