New Regiospecific Synthesis of Tri- and Tetra-Substituted Furans

被引：35

作者：

Sydnes, Leiv K. ^{[1
]}

Holmelid, Bjarte ^{[1
]}

Sengee, Myagmarsuren ^{[1
,2
]}

Hanstein, Miriam ^{[1
,3
]}

机构：

[1] Univ Bergen, Dept Chem, NO-5007 Bergen, Norway

[2] Natl Univ Mongolia, Dept Organ Chem, Ulaanbaatar 210646, Mongolia

[3] Tech Univ Dortmund, Fak Chem & Bioanorgan Chem, DE-44227 Dortmund, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 09期

关键词：

ACCELERATED CONJUGATE ADDITION; BETA-UNSATURATED KETONES; ONE-POT SYNTHESIS; LITHIUM DIMETHYLCUPRATE; ALPHA; BETA-UNSATURATED ESTERS; NUCLEOPHILIC-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; EFFICIENT SYNTHESIS; ACETYLENIC ACETALS;

D O I：

10.1021/jo9003986

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Acyloxy alpha,beta-unsaturated acetylenic ketones have been shown to react with organocuprate reagents and undergo cyclization followed by dehydration to give substituted furans as the final products. The transformation appeared to be versatile, and tri- and tetra-substituted furans were obtained, with regiochemical control in moderate to good yields. The best yields were generally obtained when the reactions were performed around -60 degrees C with substrates and cuprates containing sterically demanding substituents. The proposed mechanism for furan formation has been supported by experiments.

引用

收藏

页码：3430 / 3443

页数：14

相关论文

共 99 条

[1] Oxygenated cembranoids from a Formosan soft coral Sinulatia gibberosa [J].

Ahmed, Atallah F. ;

Wen, Zhi-Hong ;

Su, Jui-Hsin ;

Hsieh, Ya-Ting ;

Wu, Yang-Chang ;

Hu, Wan-Ping ;

Sheu, Jyh-Horng .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (02) :179-185

[2] ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

ALEXAKIS, A ;

BERLAN, J ;

BESACE, Y .

TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050

[3] Neighbouring-group influence on the ring opening of 2-aryloxymethyl-1,1,2-tribromocyclopropanes under phase-transfer conditions [J].

Bakstad, E ;

Olsen, AS ;

Sandberg, M ;

Sydnes, LK .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (07) :465-472

[4] Regiospecific ring opening of some methyl- and phenyl-substituted 1,1,2-trihalocyclopropanes to acetylenic acetals or ketals by variation of reaction conditions [J].

Bakstad, E ;

Sydnes, LK .

ACTA CHEMICA SCANDINAVICA, 1998, 52 (08) :1029-1033

[5] Rearrangement of propargylic esters:: Metal-based stereospecific synthesis of (E)- and (Z)-Knoevenagel derivatives [J].

Barluenga, Jose ;

Riesgo, Lorena ;

Vicente, Ruben ;

Lopez, Luis A. ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7772-+

[6] ELIMINATION-ADDITION .22. ADDITION OF ENOLATES TO ALLENIC SULFONIUM SALTS - NEW GENERAL FURAN SYNTHESIS [J].

BATTY, JW ;

HOWES, PD ;

STIRLING, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (01) :65-68

[7] INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES [J].

BEHLING, JR ;

BABIAK, KA ;

NG, JS ;

CAMPBELL, AL ;

MORETTI, R ;

KOERNER, M ;

LIPSHUTZ, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2641-2643

[8]

BOULARAN.G, 1967, B SOC CHIM FR, P1706

[9] CONJUGATE ADDITIONS OF GRIGNARD REAGENTS TO ALPHA,BETA-UNSATURATED ESTERS .7. ADDITIONS TO ACETYLENIC ESTERS [J].

BRETTING, C ;

MUNCHPETERSEN, J ;

JORGENSEN, PM ;

REFN, S .

ACTA CHEMICA SCANDINAVICA, 1960, 14 (01) :151-156

[10] Developments in furan syntheses [J].

Brown, RCD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852

← 1 2 3 4 5 6 7 8 9 10 →