Alkenes from alcohols by tandem hydrogen transfer and condensation

被引：38

作者：

Hall, Michael I. ^{[1
]}

Pridmore, Simon J. ^{[1
]}

Williams, Jonathan M. J. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

alcohols; alkenes; hydrogen transfer; organocatalysis; ruthenium;

D O I：

10.1002/adsc.200800338

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A ruthenium-catalysed oxidation of alcohols by hydrogen transfer has been coupled with organocatalysed condensations using pyrrolidine or piperidine, to give alpha,beta-unsaturated esters and nitroalkenes. Reactions proceed with high (E)-selectivity and provide an efficient and straightforward route alpha,beta-unsaturated compounds.

引用

收藏

页码：1975 / 1978

页数：4

相关论文

共 26 条

[1] Ruthenium-catalysed conversion of oxime ethers into nitriles [J].

Anand, Naveen ;

Owston, Nathan A. ;

Parker, Alexandra J. ;

Slatford, Paul A. ;

Williams, Jonathan M. J. .

TETRAHEDRON LETTERS, 2007, 48 (44) :7761-7763

[2] C-H activation reactions of ruthenium N-heterocyclic carbene complexes: Application in a catalytic tandem reaction involving C-C bond formation from alcohols [J].

Burling, Suzanne ;

Paine, Belinda M. ;

Nama, Devendrababu ;

Brown, Victoria S. ;

Mahon, Mary F. ;

Prior, Timothy J. ;

Pregosin, Paul S. ;

Whittlesey, Michael K. ;

Williams, Jonathan M. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1987-1995

[3] An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling [J].

Cho, CS ;

Kim, BT ;

Kim, TJ ;

Shim, SC .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9020-9022

[4] Borrowing hydrogen: a catalytic route to C-C bond formation from alcohols [J].

Edwards, MG ;

Jazzar, RFR ;

Paine, BM ;

Shermer, DJ ;

Whittlesey, MK ;

Williams, JMJ ;

Edney, DD .

CHEMICAL COMMUNICATIONS, 2004, (01) :90-91

[5] Catalytic electronic activation: Indirect "Wittig" reaction of alcohols [J].

Edwards, MG ;

Williams, JMJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4740-4743

[6] OXIDATION OF ALCOHOLS BY TRANSITION-METAL COMPLEXES .5. SELECTIVE CATALYTIC MONOALKYLATION OF ARYLACETONITRILES BY ALCOHOLS [J].

GRIGG, R ;

MITCHELL, TRB ;

SUTTHIVAIYAKIT, S ;

TONGPENYAI, N .

TETRAHEDRON LETTERS, 1981, 22 (41) :4107-4110

[7] Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].

Guillena, Gabriela ;

Ramon, Diego J. ;

Yus, Miguel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364

[8] Borrowing hydrogen in the activation of alcohols [J].

Hamid, Malai Haniti S. A. ;

Slatford, Paul A. ;

Williams, Jonathan M. J. .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1555-1575

[9] Design, synthesis, and evaluation of aza inhibitors of chorismate mutase [J].

Hediger, ME .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4995-5010

[10] APPLICATION OF THE SWERN OXIDATION TO THE MANIPULATION OF HIGHLY REACTIVE CARBONYL-COMPOUNDS [J].

IRELAND, RE ;

NORBECK, DW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2198-2200