Unexpected catalyst for Wittig-type and dehalogenation reactions

被引：69

作者：

Huang, ZZ ^{[1
]}

Tang, Y ^{[1
]}

机构：

[1] Shanghai Inst Organ Chem, State Key Lab Organometall Chen, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo025693b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel catalyst 2 for Wittig-type and dehalogenation reactions was developed. In the presence of triphenyl phosphite, a wide variety of aldehydes could react with alpha-bromoacetates to afford alpha,beta-unsaturated esters or ketones in high yields with excellent E-stereoselectivity when 1-2 mol % of compound 2 was used. Compound 2 was also an effective catalyst for reductive dehalogenation of alpha-bromocarbonyl compounds. The mechanisms for the above reactions were also proposed.

引用

页码：5320 / 5326

页数：7

共 36 条

[1] The mechanism of the haloform reaction - The preparation of mixed haloforms [J].

Aston, JG ;

Newkirk, JD ;

Dorsky, J ;

Jenkins, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1413-1416

[2]

Barrero AF, 2001, SYNLETT, P485

[3] A STUDY ON THE REDUCING ABILITIES OF TRIS(ALKYLTHIO)SILANES [J].

CHATGILIALOGLU, C ;

GUERRA, M ;

GUERRINI, A ;

SECONI, G ;

CLARK, KB ;

GRILLER, D ;

KANABUSKAMINSKA, J ;

MARTINHOSIMOES, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2427-2433

[4] Total synthesis of phorboxazole A [J].

Forsyth, CJ ;

Ahmed, F ;

Cink, RD ;

Lee, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5597-5598

[5] Gallium enolate-mediated intermolecular aldol reaction and addition reaction of α-bromoketone with imine [J].

Han, Y ;

Huang, YZ .

TETRAHEDRON LETTERS, 1998, 39 (42) :7751-7754

[6]

Hoffmann RW, 2001, ANGEW CHEM INT EDIT, V40, P1411, DOI 10.1002/1521-3773(20010417)40:8<1411::AID-ANIE1411>3.0.CO

[7]

2-U

[8] LOCAL ANESTHETICS WITH ENHANCED AFFINITY FOR PROTEINS [J].

HOLLOWOO.J ;

JANSEN, ABA ;

SOUTHGAT.PJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (05) :863-&

[9] A NOVEL ROUTE FOR THE SYNTHESIS OF ALPHA,BETA-UNSATURATED ESTERS, KETONES AND NITRILES USING DIBUTYL TELLURIDE [J].

HUANG, X ;

XIE, LH ;

WU, H .

TETRAHEDRON LETTERS, 1987, 28 (07) :801-802

[10] SYNTHETIC APPLICATIONS OF ORGANOTELLURIUM COMPOUNDS .1. A FACILE SYNTHESIS OF ALPHA,BETA-UNSATURATED ESTERS, KETONES, AND NITRILES [J].

HUANG, X ;

XIE, LH ;

WU, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4862-4864

← 1 2 3 4 →