REGIOSELECTIVE SYNTHESIS OF HIGHLY SUBSTITUTED FURANS VIA TANTALUM ALKYNE COMPLEXES

被引：22

作者：

KATAOKA, Y ^{[1
]}

TEZUKA, M ^{[1
]}

TAKAI, K ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT IND CHEM,YOSHIDA,KYOTO 60601,JAPAN

来源：

TETRAHEDRON | 1992年 / 48卷 / 17期

关键词：

TANTALUM; NIOBIUM; METAL ALKYNE COMPLEX; ISOCYANIDE; FURAN;

D O I：

10.1016/S0040-4020(01)88488-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with aldehydes followed by addition of an isocyanide in DME-PhH-THF(1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substituted furans are produced exclusively when trialkylsilylacetylenes are employed.

引用

页码：3495 / 3502

页数：8

共 47 条

[21] CARBONYL DISPLACEMENT-REACTIONS OF (C5ME5)TACL2(CO)2(THF) - STRUCTURES OF (C5ME5)TACL2(CO)2(THF), (C5ME5)TACL2(CO)(DMPE), AND (C5ME5)TACL2(METHYL ACRYLATE) [J].

KWON, D ;

CURTIS, MD .

ORGANOMETALLICS, 1990, 9 (01) :1-5

[22] CARBON-MONOXIDE CLEAVAGE BY (SILOX)3TA (SILOX=TERT-BU3SIO-) [J].

LAPOINTE, RE ;

WOLCZANSKI, PT ;

MITCHELL, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6382-6384

[23] MERCURY IN ORGANIC-CHEMISTRY .12. SYNTHESIS OF BETA-CHLORO-DELTA-ALPHA-DELTA-BETA-BUTENOLIDES VIA MERCURATION-CARBONYLATION OF PROPARGYLIC ALCOHOLS [J].

LAROCK, RC ;

RIEFLING, B ;

FELLOWS, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :131-137

[24] 5-MEMBERED HETEROAROMATIC RINGS AS INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

LIPSHUTZ, BH .

CHEMICAL REVIEWS, 1986, 86 (05) :795-819

[25] A NEW RING SYNTHESIS FOR 3-SUBSTITUTED AND POLYSUBSTITUTED FURANS - DIRECTING EFFECTS OF A 3-(ARENESULFONYL) GROUP IN METALATION AND FRIEDEL-CRAFTS PROCESSES [J].

MCCOMBIE, SW ;

SHANKAR, BB ;

GANGULY, AK .

TETRAHEDRON LETTERS, 1987, 28 (36) :4123-4126

[26]

MEYERS AI, 1974, HETEROCYCLES ORGANIC

[27] A NEW FURAN ANNELATION REACTION BY THE PALLADIUM-CATALYZED REACTION OF 2-ALKYNYL CARBONATES OR 2-(1-ALKYNYL)OXIRANES WITH BETA-KETO-ESTERS [J].

MINAMI, I ;

YUHARA, M ;

WATANABE, H ;

TSUJI, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (1-2) :225-242

[28]

NIZNIK GE, 1988, ORGANIC SYNTHSES, V6, P751

[29] A GENERAL-APPROACH TO 4-SUBSTITUTION OF 2-ALKYLFURANS [J].

NOLAN, SM ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2473-2476

[30]

Sargent M. V., 1979, COMPREHENSIVE ORGANI, V4, P693

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