Catalytic, enantioselective allylation of α-iminoesters promoted by silver(I) complexes of chiral imines

被引：26

作者：

Colombo, Federica ^{[1
]}

Annunziata, Rita ^{[1
]}

Benaglia, Maurizio ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 15期

关键词：

silver complex; homoallylic amines; enantioselective catalysis; chiral imines; chiral catalysts;

D O I：

10.1016/j.tetlet.2007.02.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective addition of allyltributylstarmane to N-protected ot-iminoesters promoted by silver(l) trifluoromethanesulfonate in the presence of chiral imine ligands was studied. After testing several chiral imines derived from 1,2-diaminocyclohexane and binaphthyl diamine a very simple experimental proc-edure was developed that allowed us to obtain optically active homoallylic amines in very high yields and enantioselectivities up to 71%. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2687 / 2690

页数：4

共 31 条

[1] Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: Chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis [J].

Albano, VG ;

Bandini, M ;

Barbarella, G ;

Melucci, M ;

Monari, M ;

Piccinelli, F ;

Tommasi, S ;

Umani-Ronchi, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :667-675

[2]

Alvaro G, 2002, SYNLETT, P651

[3] New recoverable poly(ethylene glycol)-supported C1-diamino-oligothiophene ligands for palladium-promoted asymmetric allylic alkylation (AAA) reactions [J].

Bandini, Marco ;

Benaglia, Maurizio ;

Quinto, Tommaso ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1521-1527

[4] Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone [J].

Benaglia, M ;

Benincori, T ;

Mussini, P ;

Pilati, T ;

Rizzo, S ;

Sannicolò, F .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19) :7488-7495

[5] Enantioselective addition of phenyl and alkyl acetylenes to imines catalyzed by chiral Cu(I) complexes [J].

Benaglia, M ;

Negri, D ;

Dell'Anna, G .

TETRAHEDRON LETTERS, 2004, 45 (47) :8705-8708

[6] Modular phospholane ligands in asymmetric catalysis [J].

Burk, MJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :363-372

[7] Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes [J].

Colombo, F ;

Benaglia, M ;

Orlandi, S ;

Usuelli, F ;

Celentano, G .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2064-2070

[8] Asymmetric multicomponent copper catalyzed synthesis of chiral propargylamines [J].

Colombo, Federica ;

Benaglia, Maurizio ;

Orlandi, Simonetta ;

Usuelli, Fabio .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 260 (1-2) :128-134

[9] Synthesis of new enantiomerically pure macrocycles containing phenanthroline subunits [J].

Colombo, Federica ;

Annunziata, Rita ;

Raimondi, Laura ;

Benaglia, Maurizio .

CHIRALITY, 2006, 18 (06) :446-456

[10] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

← 1 2 3 4 →