STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS - IDENTIFICATION AND ANALYSIS BY PROTON NMR AND MNDO, MM2 CALCULATIONS

被引：14

作者：

TARAKESHWAR, P ^{[1
]}

IQBAL, J ^{[1
]}

MANOGARAN, S ^{[1
]}

机构：

[1] INDIAN INST TECHNOL,DEPT CHEM,KANPUR 208016,UTTAR PRADESH,INDIA

来源：

TETRAHEDRON | 1991年 / 47卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)80924-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl acetoacetate and terminal olefins react in the presence of cobalt(II) acetate and oxygen to give 5-alkyl-2-hydroxy-2-methyl-3-methoxycarbonyl tetrahydrofurans in a highly stereoselective manner. Proton NMR, semiempirical MNDO and empirical MM2 methods are used to identify the particular diastereomer and the energetics of the different isomers are discussed.

引用

页码：297 / 304

页数：8

共 13 条

[1]

BARTLETT PA, 1984, ASYMMETRIC SYNTHESIS, V3, pCH6

[2]

BARTLETT PA, 1980, TETRAHEDRON, V36, P2

[3]

BOIVIN TLB, 1987, TETRAHEDRON, V43, P4709

[4]

Clark T., 1985, HDB COMPUTATIONAL CH

[5] MN(III)-PROMOTED ANNULATION OF ENOL ETHERS AND ESTERS TO FUSED OR SPIRO 2-CYCLOPENTENONES [J].

COREY, EJ ;

GHOSH, AK .

TETRAHEDRON LETTERS, 1987, 28 (02) :175-178

[6] NEW AND GENERAL-SYNTHESIS OF POLYCYCLIC GAMMA-LACTONES BY DOUBLE ANNULATION [J].

COREY, EJ ;

KANG, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5384-5385

[7] OXIDATION BY METAL SALTS .4. A NEW METHOD FOR PREPARATION OF GAMMA-LACTONES BY REACTION OF MANGANIC ACETATE WITH OLEFINS [J].

HEIBA, EI ;

DESSAU, RM ;

KOEHL, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5905-&

[8] COBALT(II) ACETATE PROMOTED ADDITION OF ACETOACETATE TO TERMINAL OLEFINS - A HIGHLY STEREOSELECTIVE SYNTHESIS OF 5-ALKYL-2-HYDROXY-2-METHYL-3-METHOXYCARBONYL TETRAHYDROFURANS [J].

IQBAL, J ;

KUMAR, TKP ;

MANOGARAN, S .

TETRAHEDRON LETTERS, 1989, 30 (35) :4701-4702

[9]

Ruff M. D., 1982, POLYETHER ANTIBIOTIC

[10]

SEMPLE JE, 1980, HETEROCYCLES, V14, P1825

← 1 2 →