Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

被引：137

作者：

Goossen, LJ ^{[1
]}

Paetzold, J ^{[1
]}

Koley, D ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 06期

关键词：

D O I：

10.1039/b211277a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic activity of commercially available, air and water stable ruthenium complexes in the addition of carboxylic acids to terminal alkynes was found to be drastically enhanced by the addition of small quantities of base. Moreover, the regioselectivity of the reaction can be controlled by the choice of the base so that both the Markovnikov (Na2CO3) and the anti-Markovnikov products (DMAP) are now easily accessible in excellent selectivities.

引用

页码：706 / 707

页数：2

共 30 条

[21] RUTHENIUM-CATALYZED SELECTIVE ADDITION OF CARBOXYLIC-ACIDS TO ALKYNES - A NOVEL SYNTHESIS OF ENOL ESTERS [J].

MITSUDO, T ;

HORI, Y ;

YAMAKAWA, Y ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2230-2239

[22] PROPERTIES OF ENOL ESTERS .1. POLYMERIZATION OF ACETOXYALKENES AND DIELECTRIC MEASUREMENTS OF OBTAINED POLYMERS [J].

MONTHEARD, JP ;

CAMPS, M ;

SEYTRE, G ;

GUILLET, J ;

DUBOIS, JC .

ANGEWANDTE MAKROMOLEKULARE CHEMIE, 1978, 72 (OCT) :45-55

[23] A PRACTICAL CYCLOPROPANATION METHOD USING DIRECT GENERATION OF ORGANOZINC CARBENOIDS FROM CARBONYL-COMPOUNDS [J].

MOTHERWELL, WB ;

ROBERTS, LR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (21) :1582-1583

[24] DIPOLAR CYCLOADDITION OF RHODIUM CARBENOIDS WITH VINYL ESTERS - TOTAL SYNTHESIS OF PONGAMOL AND LANCEOLATIN-B [J].

PIRRUNG, MC ;

LEE, YR .

TETRAHEDRON LETTERS, 1994, 35 (34) :6231-6234

[25] ADDITION OF CARBOXYLIC-ACIDS TO ALKYNES CATALYZED BY RUTHENIUM COMPLEXES - VINYL ESTER FORMATION [J].

ROTEM, M ;

SHVO, Y .

ORGANOMETALLICS, 1983, 2 (11) :1689-1691

[26] ASYMMETRIC HYDROFORMYLATION OF VINYL-ACETATE BY USE OF CHIRAL BIS(TRIARYLPHOSPHITE) - RHODIUM(I) COMPLEXES [J].

SAKAI, N ;

NOZAKI, K ;

MASHIMA, K ;

TAKAYA, H .

TETRAHEDRON-ASYMMETRY, 1992, 3 (05) :583-586

[27] CHEMISTRY OF ORGANO HALOGENIC MOLECULES .100. COMPARATIVE BEHAVIOR OF XENON DIFLUORIDE AND CESIUM FLUOROXYSULFATE IN THE FLUORINATION OF ENOL ACETATES AND KETONES [J].

STAVBER, S ;

SKET, B ;

ZAJC, B ;

ZUPAN, M .

TETRAHEDRON, 1989, 45 (18) :6003-6010

[28]

TIETZE LF, 1994, SYNLETT, P509

[29] HIGHLY CONVENIENT ELECTROLYSIS PROCEDURE FOR THE PREPARATION OF ALPHA-HALOGENATED KETONES AND ACETALS FROM ENOL ACETATES, ENOL ETHERS, AND SILYL ENOL ETHERS [J].

TORII, S ;

INOKUCHI, T ;

MISIMA, S ;

KOBAYASHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13) :2731-2735

[30] PHOTOCHEMICAL SYNTHON FOR 5-URACIL CARBANION - APPLICATION TO DIRECT FUNCTIONALIZATION OF UNPROTECTED URACILS [J].

WEXLER, A ;

BALCHUNIS, RJ ;

SWENTON, JS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) :601-602

← 1 2 3 →