FACILE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS BY ENOLATE OXIDATION WITH DIMETHYLDIOXIRANE

被引：48

作者：

GUERTIN, KR ^{[1
]}

CHAN, TH ^{[1
]}

机构：

[1] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2K6,QUEBEC,CANADA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(00)74865-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct oxidation of enolates with dimethyldioxirane (as a solution in acetone) provides the alpha-hydroxy derivatives in excellent yield.

引用

页码：715 / 718

页数：4

共 26 条

[1] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS
ADAM, W
HADJIARAPOGLOU, L
NESTLER, B
[J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 331 - 334
[2] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS
ADAM, W
CHAN, YY
CREMER, D
GAUSS, J
SCHEUTZOW, D
SCHINDLER, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2800 - 2803
[3] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[4] EPOXIDATION OF SILYL ENOL ETHERS, PHTHALIDES, AND ENOL ESTERS BY DIMETHYLDIOXIRANE
ADAM, W
HADJIARAPOGLOU, L
WANG, XH
[J]. TETRAHEDRON LETTERS, 1989, 30 (47) : 6497 - 6500
[5] EPOXIDATION OF GAMMA-METHYLENE-GAMMA-BUTYROLACTONES BY DIMETHYLDIOXIRANE
ADAM, W
HADJIARAPOGLOU, L
JAGER, V
SEIDEL, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (32) : 4223 - 4226
[6] GENERAL SYNTHETIC ROUTES TO DIARENE OXIDES OF POLYCYCLIC AROMATIC-HYDROCARBONS
AGARWAL, SK
BOYD, DR
JENNINGS, WB
MCGUCKIN, RM
OKANE, GA
[J]. TETRAHEDRON LETTERS, 1989, 30 (01) : 123 - 126
[7] PREPARATION OF THE 8,9-EPOXIDE OF THE MYCOTOXIN AFLATOXIN-B1 - THE ULTIMATE CARCINOGENIC SPECIES
BAERTSCHI, SW
RANEY, KD
STONE, MP
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7929 - 7931
[8] COMPOUNDS RELATED TO STEROID HORMONES .9. OXYGENATION OF STEROID KETONES IN STRONGLY BASIC MEDIUM - NEW METHOD OF PREPARATION OF 17ALPHA-HYDROXYPREGNAN-20-ONES
BAILEY, EJ
TEMPLETON, JF
ELKS, J
BARTON, DHR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAY): : 1578 - &
[9] DIMETHYLDIOXIRANE - MECHANISM OF BENZALDEHYDE OXIDATION
BAUMSTARK, AL
BEESON, M
VASQUEZ, PC
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5567 - 5570
[10] AN ASYMMETRIC-SYNTHESIS OF (+)-KJELLMANIANONE
BOSCHELLI, D
SMITH, AB
STRINGER, OD
JENKINS, RH
DAVIS, FA
[J]. TETRAHEDRON LETTERS, 1981, 22 (44) : 4385 - 4388

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