AN EFFICIENT METHOD FOR THE VICINAL ACYLATION OF UNACTIVATED OLEFINS USING KETENIMINIUM SALTS DERIVED FROM PROTECTED ALPHA-HYDROXYACIDS OR ALPHA-AMINO-ACIDS

被引：32

作者：

GENICOT, C ^{[1
]}

GOBEAUX, B ^{[1
]}

GHOSEZ, L ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN SYNTH LAB,PL L PASTEUR 1,B-1348 LOUVAIN,BELGIUM

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)79386-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Keteniminium salts derived from O-methylglycolic or N-tosylsarcosine amides cycloadd to olefins to give good yields of the corresponding cyclobutanones which undergo regiospecific Baeyer-Villiger oxidation to form gamma-butyrolactones.

引用

页码：3827 / 3830

页数：4

共 19 条

[1] INTRAMOLECULAR [2 + 2] CYCLOADDITIONS OF KETENE IMINIUM SALTS TO CARBON CARBON DOUBLE-BONDS [J].

BRADY, WT ;

GIANG, YSF ;

WENG, L ;

DAD, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2216-2220

[2] CYCLO-ADDITIONS OF (ARYLALKYLAMINO)KETENES WITH CYCLOALKENES [J].

BRADY, WT ;

GU, YQ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2834-2838

[3]

COSSEMENT E, 1974, TETRAHEDRON LETT, P997

[4]

DOMINH T, 1970, J AM CHEM SOC, V92, P1766

[5]

Falmagne J. B., 1990, ORG SYNTH, V69, P199

[6] [2+2] CYCLOADDITION OF OPTICALLY-ACTIVE KETENES - SYNTHESIS OF (-)-BLASTMYCINONE [J].

FRATER, G ;

MULLER, U ;

GUNTHER, W .

HELVETICA CHIMICA ACTA, 1986, 69 (08) :1858-1861

[7]

GHOSEZ L, 1979, STEREOSELECTIVE SYNT, P93

[8]

GOBEAUX B, 1988, HETEROCYCLES, V28, P1

[9] A SHORT, ECONOMICAL, AND STEREOSELECTIVE ROUTE TO PROSTAGLANDINS BY VICINAL ALKYLATION OF CYCLOPENTADIENE [J].

GOLDSTEIN, S ;

VANNES, P ;

HOUGE, C ;

FRISQUEHESBAIN, AM ;

WIAUXZAMAR, C ;

GHOSEZ, L ;

GERMAIN, G ;

DECLERCQ, JP ;

VANMEERSSCHE, M ;

ARRIETA, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4616-4618

[10]

GREEN AE, 1985, J ORG CHEM, V50, P1972

← 1 2 →