Rhodium-catalyzed conjugate addition-enantioselective protonation:: The synthesis of α,α'-dibenzyl esters

被引：46

作者：

Frost, Christopher G. ^{[1
]}

Penrose, Stephen D.

Lambshead, Kim

Raithby, Paul R.

Warren, John E.

GleaveO, Robert

机构：

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

[2] GlaxoSmithKline Inc, Neurol & Gastrointestinal Ctr Excellence Drug Dis, Harlow CM19 5AW, Essex, England

[3] CCLRC, Daresbury Lab, Warrington WA4 4AD, Cheshire, England

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 11期

关键词：

D O I：

10.1021/ol070603g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodium-catalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched alpha, alpha'-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor.

引用

页码：2119 / 2122

页数：4

共 28 条

[1] Microwave chemistry: Out of the kitchen [J].

Adam, D .

NATURE, 2003, 421 (6923) :571-572

[2] Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes [J].

Bigi, F ;

Carloni, S ;

Ferrari, L ;

Maggi, R ;

Mazzacani, A ;

Sartori, G .

TETRAHEDRON LETTERS, 2001, 42 (31) :5203-5205

[3] Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aidol cyclization [J].

Bocknack, BM ;

Wang, LC ;

Krische, MJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5421-5424

[4] MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].

CADDICK, S .

TETRAHEDRON, 1995, 51 (38) :10403-10432

[5] Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].

Cauble, DF ;

Gipson, JD ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111

[6] Enantioselective rhodium-catalysed addition of boronic acids using C2-symmetric aryl diphosphite ligands [J].

Chapman, CJ ;

Wadsworth, KJ ;

Frost, CG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) :206-211

[7] Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].

Darses, S ;

Genet, JP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327

[8] Recent advances into the enantioselective protonation of prostereogenic enol derivatives [J].

Eames, J ;

Weerasooriya, N .

TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :1-24

[9] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[10] Rhodium-catalysed addition of organotrialkoxysilanes to α-substituted acrylic esters [J].

Hargrave, Jonathan D. ;

Herbert, Jennifer ;

Bish, Gerwyn ;

Frost, Christopher G. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3235-3241

← 1 2 3 →