Regiospecific acylation of acetals.: A convenient method to obtain β-methoxyvinyl trichloromethyl ketones

被引：69

作者：

Martins, MAP ^{[1
]}

Bastos, GP

Bonacorso, HG

Zanatta, N

Flores, AFC

Siqueira, GM

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Fed Pelotas, Dept Quim Organ, BR-96040160 Pelotas, RS, Brazil

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(99)00672-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemistry of the acylation of enol ethers, generated in situ, from acetals of unsymmetrical ketones is reported. These results demonstrate a convenient one-pot method to obtain a series of beta-methoxyvinyl trichloromethyl ketones [CCl3COCH=C(OMe)R, where R=Et, n-Bu, i-Pr, (CH2)(2)C(OMe)=CHC(O)CCl3 and (CH2)(5)CO2CH3)] in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4309 / 4312

页数：4

共 28 条

[1] A convenient method for the synthesis of 2-trichloromethyl-4-p-substituted-phenyl-3H-1,5-benzodiazepines. [J].

Bonacorso, HG ;

Bittencourt, ST ;

Wastowski, AD ;

Wentz, AP ;

Zanatta, N ;

Martins, MAP .

TETRAHEDRON LETTERS, 1996, 37 (51) :9155-9156

[2] HALOACETYLATED ENOL ETHERS .2. SYNTHESIS OF 5-TRIFLUOROMETHYLPYRAZOLES [J].

BRAIBANTE, MEF ;

CLAR, G ;

MARTINS, MAP .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (04) :1159-1160

[3]

CAZEAW P, 1980, J ORGANOMETALLIC C C, V9, P201

[4] ENOL ETHERS .14. ACYLATION OF KETO ENOL ETHERS WITH MALONYL DICHLORIDE - A NEW SYNTHESIS OF PHLOROGLUCINOLS [J].

EFFENBERGER, F ;

SCHONWALDER, KH .

CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (11) :3270-3279

[5]

Fischer P., 1988, QUIM NOVA, V11, P348

[6]

FISCHER P, 1980, CHEM FUNCTIONAL 2 SE

[7]

HOJO M, 1986, SYNTHESIS-STUTTGART, P1013

[8]

HOJO M, 1986, SYNTHESIS-STUTTGART, P1016

[9] ELECTROPHILIC SUBSTITUTIONS OF OLEFINIC HYDROGENS .2. ACYLATION OF VINYL ETHERS AND N-VINYL AMIDES [J].

HOJO, M ;

MASUDA, R ;

KOKURYO, Y ;

SHIODA, H ;

MATSUO, S .

CHEMISTRY LETTERS, 1976, (05) :499-502

[10]

HOUSE HO, 1963, J ORG CHEM, V28, P3362, DOI 10.1021/jo01047a022

← 1 2 3 →