Palladium-catalyzed asymmetric allylic alkylation with an enamine as the nucleophilic reagent

被引：66

作者：

Liu, Delong ^{[1
]}

Xie, Fang ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Technol, Shanghai, Peoples R China

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 43期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetlet.2007.08.119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enamine can serve as a good nucleophile for palladium-catalyzed asymmetric allylic alkylation, avoiding the use of an unstablilized ketone enolate formed by strong bases. In the presence of a palladium complex of chiral metallocene-based phosphino-oxazoline ligands, the reaction was carried out smoothly with high catalytic activity and excellent enantioselectivity. Different distances between the two Cp rings of ferrocene and ruthenocene affected the catalytic behavior in the reaction. Furthermore, high catalytic activity and good enantio selectivity were also afforded by the ferrocene-based diphosphine ligands with only planar chirality. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：7591 / 7594

页数：4

共 66 条

[1] Comparing chiral ferrocenyl and ruthenocenyl ligands: How subtle structural changes influence their performance in asymmetric catalysis [J].

Abbenhuis, HCL ;

Burckhardt, U ;

Gramlich, V ;

Martelletti, A ;

Spencer, J ;

Steiner, I ;

Togni, A .

ORGANOMETALLICS, 1996, 15 (06) :1614-1621

[2]

[Anonymous], FERROCENES

[3] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[4] Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers [J].

Belanger, Etienne ;

Cantin, Katy ;

Messe, Olivier ;

Tremblay, Melanie ;

Paquin, Jean-Francois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1034-1035

[5] Synthesis of novel 1,1′-bis(oxazolinyl)metallocenes and their application in the asymmetric phenyl transfer from organozincs to aldehydes [J].

Bolm, C ;

Hermanns, N ;

Kesselgruber, M ;

Hildebrand, JP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :157-161

[6] New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates [J].

Braun, M ;

Meier, T .

SYNLETT, 2006, (05) :661-676

[7]

Braun M, 2000, ANGEW CHEM INT EDIT, V39, P3494, DOI 10.1002/1521-3773(20001002)39:19<3494::AID-ANIE3494>3.0.CO

[8]

2-4

[9] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (22) :4113-4115

[10] THE REGIOSELECTIVITIES AND STEREOSELECTIVITIES OF THE REACTION OF ALLYL ACETATES AND SILYL KETENE ACETALS CATALYZED BY PD(0) COMPLEXES - A NEW ROUTE TO CYCLOPROPANE DERIVATIVES [J].

CARFAGNA, C ;

MARIANI, L ;

MUSCO, A ;

SALLESE, G ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3924-3927

← 1 2 3 4 5 6 7 →