Bifunctional copper catalysts. A one step synthesis of bicyclic ethers starting from alpha,beta-unsaturated ketones

被引：16

作者：

Ravasio, N

Leo, V

Babudri, F

Gargano, M

机构：

[1] Centro C.N.R. MISO, Dipto. di Chim. dell'Univ., I-70126 Bari

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(97)01631-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, one pot synthesis of bicyclic ethers starting from alpha,beta-unsaturated ketones containing an additional isolated olefinic bond is proposed. It relies on highly chemoselective hydrogenation of the enone group to the corresponding alcohol in the presence of supported copper catalysts, and on the presence of acidic sites on the catalyst support activating the double bond as a carbocation. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：7103 / 7106

页数：4

相关论文

共 11 条

[1] NMR ASSIGNMENTS FOR SOME 2-SUBSTITUTED 2,6,6-TRIMETHYL-7-OXA-BICYCLO[3.2.1]OCTANES (DIHYDROPINOLS) [J].

CARMAN, RM ;

FLETCHER, MT ;

LAMBERT, LK .

MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (03) :271-272

[2] Chiral syntheses of edulans I, II and dihydroedulans I, II and absolute configurations of edulans I, II [J].

Honda, T ;

Yamauchi, A ;

Tsubuki, M ;

Matsumoto, T .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :837-839

[3]

MASUDA H, 1961, Patent No. 65879

[4] STEREOCHEMISTRY ODOR RELATIONSHIPS IN 1-DECALONE SERIES AND THEIR OXA-ANALOGS [J].

OHLOFF, G ;

GIERSCH, W ;

SCHULTEELTE, KH ;

VIAL, C .

HELVETICA CHIMICA ACTA, 1976, 59 (04) :1140-1157

[5] Cu/SiO2: An improved catalyst for the chemoselective hydrogenation of alpha,beta-unsaturated ketones [J].

Ravasio, N ;

Antenori, M ;

Gargano, M ;

Mastrorilli, P .

TETRAHEDRON LETTERS, 1996, 37 (20) :3529-3532

[6] CHEMOSELECTIVITY AND REGIOSELECTIVITY IN THE HYDROGENATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS PROMOTED BY CU/AL2O3 [J].

RAVASIO, N ;

ANTENORI, M ;

GARGANO, M ;

ROSSI, M .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 74 (1-3) :267-274

[7] SYNTHESIS AND ENATIODIFFERENTIATION OF ISOMERIC 3,5,6,8A-TETRAHYDRO-2,5,5,8A-TETRAMETHYL-2H-1-BENZOPYRANS (EDULAN-I AND EDULAN-II) [J].

SCHMIDT, G ;

FULL, G ;

WINTERHALTER, P ;

SCHREIER, P .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (01) :185-188

[8] DIASTEREOSELECTIVE ODOR PERCEPTION OF ALCOHOLS IN THE IONONE SERIES [J].

SCHULTEELTE, KH ;

GIERSCH, W ;

WINTER, B ;

PAMINGLE, H ;

OHLOFF, G .

HELVETICA CHIMICA ACTA, 1985, 68 (07) :1961-1985

[9] PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .13. A SYNTHETIC STUDY OF (-)-DIHYDROEDULAN-II AND RELATED-COMPOUNDS [J].

SUGAI, T ;

YOKOCHI, T ;

WATANABE, N ;

OHTA, H .

TETRAHEDRON, 1991, 47 (35) :7227-7236

[10] PINOL DERIVATIVES FROM LITHIUM ALUMINUM-HYDRIDE REDUCTION OF CINEOLE CHLOROHYDRIN [J].

WOLINSKY, J ;

THORSTENSON, JH ;

VOGEL, MK .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) :253-257