Highly regio-, diastereo-, and enantioselective Pd-catalyzed allylic alkylation of acyclic ketone enolates with monosubstituted allyl substrates

被引：145

作者：

Zheng, Wen-Hua ^{[1
]}

Zheng, Bao-Hui ^{[1
]}

Zhang, Yan ^{[1
]}

Hou, Xue-Long ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 25期

关键词：

D O I：

10.1021/ja071098l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-catalyzed asymmetric allylic alkylation reactions of acyclic ketones with monosubstituted allyl substrates using 1,1'-P,N-ferrocene with H as substituent on the oxazoline ring as ligand gave products having two chiral centers with high yields and with high regio-, diastereo-, and enantioselectivities, with the ratio of branched and linear products being 98:2, anti:syn ratio for branched products being 7-21:1, and ee for the anti-products being 92-99%.

引用

页码：7718 / +

页数：3

共 36 条

[1] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

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

[2] 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

[3]

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

[4]

2-4

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

Burger, EC ;

Tunge, JA .

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

[6] Asymmetric catalysis with chiral ferrocene ligands [J].

Dai, LX ;

Tu, T ;

You, SL ;

Deng, WP ;

Hou, XL .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (09) :659-667

[7] Regio- and diastereoselective rhodium-catalyzed allylic substitution with acyclic α-alkoxy-substituted copper(I) enolates:: Stereodivergent approach to 2,3,6-trisubstituted dihydropyrans [J].

Evans, PA ;

Lawler, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8642-8643

[8] Regioselective and enantiospecific rhodium-catalyzed intermolecular allylic etherification with ortho-substituted phenols [J].

Evans, PA ;

Leahy, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :5012-5013

[9] Iridium-catalyzed regio- and enantioselective allylation of ketone enolates [J].

Graening, T ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17192-17193

[10] 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

← 1 2 3 4 →