Reaction of heterocyclic allyl sulphides with ethyl diazoacetate: A simple method for the synthesis of conjugated dienoic esters

被引：5

作者：

Calo, V

Nacci, A

Fiandanese, V

Volpe, A

机构：

[1] CNR Ctro. Stud. Metodologie Innov., Sintesi Organiche, Università di Bari, 4-70126 Bari, via Orabona

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(97)00587-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heterocyclic allyl sulphides 1-6 react with an excess of ethyl diazoacetate in the presence of copper(I)exafluorophosphate acetonitrile complex in dichloromethane under mild conditions to give, through the formation of homoallylic sulphides intermediates, conjugated dienoic esters in high yields. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：3289 / 3290

页数：2

共 12 条

[1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS
ADAMS, J
SPERO, DM
[J]. TETRAHEDRON, 1991, 47 (10-11) : 1765 - 1808
[2] YLIDE FORMATION AND REARRANGEMENT IN REACTION OF CARBENE WITH DIVALENT SULFUR-COMPOUNDS
ANDO, W
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (05) : 179 - 185
[3] Copper-mediated regio- and enantio-selective cross-coupling of heterocyclic allyl sulphides with organomagnesium compounds: A case of 1,7-relative stereogenesis
Calo, V
Nacci, A
Fiandanese, V
[J]. TETRAHEDRON, 1996, 52 (32) : 10799 - 10810
[4] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
DOYLE, MP
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
[5] CLAISEN REARRANGEMENT OF ALLYL ESTERS
IRELAND, RE
MUELLER, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) : 5897 - &
[6] YLIDE FORMATION FROM THE REACTION OF CARBENES AND CARBENOIDS WITH HETEROATOM LONE PAIRS
PADWA, A
HORNBUCKLE, SF
[J]. CHEMICAL REVIEWS, 1991, 91 (03) : 263 - 309
[7] PADWA A, 1994, ANGEW CHEM INT EDIT, V33, P1797, DOI 10.1002/anie.199417971
[8] ONE-FLASK, REGIOSPECIFIC CONVERSIONS OF ALLYLIC ALCOHOLS INTO 2-CARBON-EXTENDED, CONJUGATED DIENOATE ESTERS - USE OF A NEW SULFINYL ORTHOESTER
POSNER, GH
CROUCH, RD
KINTER, CM
CARRY, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 6981 - 6987
[9] ASYMMETRIC TOTAL SYNTHESIS OF AN A-RING PRECURSOR TO HORMONALLY ACTIVE 1-ALPHA,25-DIHYDROXYVITAMIN-D3
POSNER, GH
KINTER, CM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 3967 - 3969
[10] VEDEJS E, 1977, TETRAHEDRON LETT, P1241

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