Synthesis of tetrasubstituted furans by sequential SmI2-promoted reduction and Pd-catalyzed cyclization

被引：26

作者：

Aurrecoechea, JM ^{[1
]}

Pérez, E ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ, E-48080 Bilbao, Spain

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(01)00574-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrasubstituted furans are obtained in a one-pot, two-step sequence comprising Sml(2)-promoted reduction of a readily available 4,5-epoxyalk-2-ynyl ester followed by Pd(0)-promoted cyclization of the resulting 2,3,3-trien-1-ol in the presence of an aryl halide or triflate. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3839 / 3841

页数：3

共 33 条

[1] IODOENOLCYCLIZATION .3. A GENERAL-APPROACH TO TETRASUBSTITUTED FURANS FROM 2-ALKENYL-1,3-DICARBONYL COMPOUNDS
ANTONIOLETTI, R
CECCHINI, C
CIANI, B
MAGNANTI, S
[J]. TETRAHEDRON LETTERS, 1995, 36 (49) : 9019 - 9022
[2] THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES
ARCADI, A
CACCHI, S
LAROCK, RC
MARINELLI, F
[J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2813 - 2816
[3] A palladium-catalyzed domino reaction of 3-acetyl-5-hexyn-2-one with aryl iodides under carbon monoxide
Arcadi, A
Rossi, E
[J]. TETRAHEDRON LETTERS, 1996, 37 (37) : 6811 - 6814
[4] Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction-elimination and Pd(II)-catalyzed cycloisomerization
Aurrecoechea, JM
Pérez, E
Solay, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) : 564 - 569
[5] Heterocycles via cyclization of alkynes promoted by organopalladium complexes
Cacchi, S
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 42 - 64
[6] SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED BUTA-1,2,3-TRIENES
CHOW, HF
CAO, XP
LEUNG, MK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (03): : 193 - 196
[7] Dean F. M., 1984, COMPREHENSIVE HETERO, V4, P531, DOI DOI 10.1016/B978-008096519-2.00060-6
[8] Donnelly D.M. X., 1984, COMPREHENSIVE HETERO, V4, P657, DOI DOI 10.1016/B978-008096519-2.00062-X
[9] Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones
Forgione, P
Wilson, PD
Fallis, AG
[J]. TETRAHEDRON LETTERS, 2000, 41 (01) : 17 - 20
[10] SYNTHESIS OF SUBSTITUTED FURANS BY PALLADIUM-CATALYZED CYCLIZATION OF ACETYLENIC KETONES
FUKUDA, Y
SHIRAGAMI, H
UTIMOTO, K
NOZAKI, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5816 - 5819

← 1 2 3 4 →