Microwave-assisted, regioselective, petasis olefination of unsymmetrical oxalates. Formation of pyruvate-based enol ethers and enamines

被引：13

作者：

Cook, MJ ^{[1
]}

Fleming, DW ^{[1
]}

Gallagher, T ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 02期

关键词：

petasis reagent; olefination; pyruvates; enamines; enol ethers;

D O I：

10.1016/j.tetlet.2004.11.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Petasis olefination Of unsymmetrical oxalates and oxalate monoesters/monoamides (tert-BuO2CC(O)X. where X = OR, NR2) is highly regioselective and provides pyruvate-based enol ether and enamine derivatives. The olefination steep occurs under conventional thermal conditions, but is dramatically iniproved-shorter reaction tinies and higher vields-wheen proinowed by microwave irradiation. (C) 2004 Elsevier Ltd. All rialits reserved.

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页码：297 / 300

页数：4

相关论文

共 24 条

[1]

Barluenga J, 1997, SYNTHESIS-STUTTGART, P967

[2] ALPHA-ALKOXYACRYLIC ACIDS FROM ALPHA-KETO ACIDS [J].

BATES, RB ;

CALDERA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6920-6921

[3] Studies directed to the synthesis of the unusual cardiotoxic agent kalmanol. Enantioselective construction of the advanced tetracyclic 7-oxy-5,6-dideoxy congener [J].

Borrelly, S ;

Paquette, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (04) :727-740

[4] The chemistry of isopropenyl glycopyranosides. Transglycosylations and other reactions [J].

Chenault, HK ;

Castro, A ;

Chafin, LF ;

Yang, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5024-5031

[5] HYDROLYSIS OF O-ISOPROPENYL GLUCOPYRANOSIDES INVOLVES C-PROTONATION AND ALKENYL ETHER CLEAVAGE AND EXHIBITS A KINETIC INFLUENCE OF ANOMERIC CONFIGURATION [J].

CHENAULT, HK ;

CHAFIN, LF .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6167-6169

[6] Kinetic study of microwave-assisted Wittig reaction of stabilised ylides with aromatic aldehydes [J].

Frattini, S ;

Quai, M ;

Cereda, E .

TETRAHEDRON LETTERS, 2001, 42 (39) :6827-6829

[7] Titanium reagents for the alkylidenation of carboxylic acid and carbonic acid derivatives [J].

Hartley, RC ;

McKiernan, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2763-2793

[8] Ring-closing metathesis of α-ester-substituted enol ethers:: application to the shortest synthesis of KDO [J].

Hekking, KFW ;

van Delft, FL ;

Rutjes, FPJT .

TETRAHEDRON, 2003, 59 (35) :6751-6758

[9] Mechanistic study of ester olefinations using dimethyltitanocene [J].

Hughes, DL ;

Payack, JF ;

Cai, DW ;

Verhoeven, TR ;

Reider, PJ .

ORGANOMETALLICS, 1996, 15 (02) :663-667

[10] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].

MARYANOFF, BE ;

REITZ, AB .

CHEMICAL REVIEWS, 1989, 89 (04) :863-927