BETA-ALKYL AND BETA-ALKYL-ALPHA-HYDROXY CARBOXYLIC-ACID DERIVATIVES FROM RADICAL OR IONIC 1,4 ADDITION OF DIALKYLALUMINUM CHLORIDES TO ALPHA,BETA-UNSATURATED N-ACYL URETHANES

被引：46

作者：

RUCK, K

KUNZ, H

机构：

[1] Institut Für Organische Chemie, Universität Johann-, Mainz, W-6500

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 06期

关键词：

D O I：

10.1002/anie.199106941

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Et2AlCl reacts with chiral alpha,beta-unsaturated N-acyloxazolidones 1 exclusively ionically, Me2AlCl, on the other hand, exclusively radically with 1,4 addition of the alkyl residue to give beta-branched carboxylic acid derivatives. The intermediary aluminum enolates formed from Me2AlCl after methyl transfer can react with triplet oxygen to give alpha-hydroxy-beta-methylcarboxylic acid derivatives.

引用

页码：694 / 696

页数：3

共 22 条

[1] AN ASYMMETRIC-SYNTHESIS OF (+)-KJELLMANIANONE
BOSCHELLI, D
SMITH, AB
STRINGER, OD
JENKINS, RH
DAVIS, FA
[J]. TETRAHEDRON LETTERS, 1981, 22 (44) : 4385 - 4388
[2] COOK AH, 1949, J CHEM SOC, P1026
[3] PEROXIDES OF ELEMENTS OTHER THAN CARBON .14. MECHANISM OF AUTOXIDATION OF ORGANIC COMPOUNDS OF LITHIUM MAGNESIUM ZINC CADMIUM AND ALUMINIUM
DAVIES, AG
ROBERTS, BP
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (09): : 1074 - &
[4] PEROXIDES OF ELEMENTS OTHER THAN CARBON .10. ORGANOPEROXYALUMINIUM COMPOUNDS AS INTERMEDIATES IN REDOX REACTIONS
DAVIES, AG
HALL, CD
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (FEB): : 1192 - &
[5] SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES
DAVIS, FA
VISHWAKARMA, LC
BILLMERS, JM
FINN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) : 3241 - 3243
[6] DAVIS FA, 1989, TETRAHEDRON, V45, P5729
[7] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES
EVANS, DA
CHAPMAN, KT
BISAHA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1238 - 1256
[8] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS
EVANS, DA
MORRISSEY, MM
DOROW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) : 4346 - 4348
[9] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE
EVANS, DA
BRITTON, TC
ELLMAN, JA
[J]. TETRAHEDRON LETTERS, 1987, 28 (49) : 6141 - 6144
[10] ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-ESTERS VIA ESTER ENOLATES
GAMBONI, R
MOHR, P
WAESPESARCEVIC, N
TAMM, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (02) : 203 - 206

← 1 2 3 →