α-Hydroxylation of β-dicarbonyl compounds

被引：139

作者：

Christoffers, J ^{[1
]}

Baro, A ^{[1
]}

Werner, T ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 2-3期

关键词：

atom economy; carbonyl compounds; oxidation; oxygen; reagents; synthetic methods;

D O I：

10.1002/adsc.200303140

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The most convenient and direct route to alpha-hydroxy-beta-dicarbonyl compounds is the oxidation of readily accessible 1,3-dicarbonyls. Hence, this type of oxidation is an intensively investigated field. In this short review, we present and compare alpha-hydroxylations using various oxidants such as peracids (Rubottom oxidation), dimethyldioxirane or molecular oxygen. From an economical and ecological point of view, metal-catalyzed air oxidations are optimal at least for cyclic beta-dicarbonyls. For asymmetric alpha-hydroxylations only chiral sulfonyloxaziridines are available to date. Thus, there is still a need for significant development in this area.

引用

页码：143 / 151

页数：9

共 79 条

[31] Total synthesis of (±)-ginkgolide B
Crimmins, MT
Pace, JM
Nantermet, PG
Kim-Meade, AS
Thomas, JB
Watterson, SH
Wagman, AS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) : 10249 - 10250
[32] The total synthesis of (±)-ginkgolide B
Crimmins, MT
Pace, JM
Nantermet, PG
Kim-Meade, AS
Thomas, JB
Watterson, SH
Wagman, AS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (35) : 8453 - 8463
[33] A NEW SYNTHESIS OF METHYL ALPHA-ACETOLACTATE BASED ON THIAZOLIUM CHEMISTRY AND MODELED ON THE ENZYMATIC-SYNTHESIS OF ALPHA-ACETOLACTATE CATALYZED BY ACETOLACTATE SYNTHASE
CROUT, DHG
LEE, ER
PEARSON, DPJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (04) : 331 - 333
[34] A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)-(-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL - A KEY INTERMEDIATE IN THE SYNTHESIS OF ANTHRACYCLINONES
DAVIS, FA
KUMAR, A
CHEN, BC
[J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 867 - 870
[35] CHEMISTRY OF OXAZIRIDINES .2. IMPROVED SYNTHESIS OF 2-SULFONYLOXAZIRIDINES
DAVIS, FA
STRINGER, OD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) : 1774 - 1775
[36] ASYMMETRIC-SYNTHESIS OF THE AB RING SEGMENTS OF DAUNOMYCIN AND 4-DEMETHOXYDAUNOMYCIN
DAVIS, FA
CLARK, C
KUMAR, A
CHEN, BC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 1184 - 1190
[37] Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
Davis, FA
Liu, H
Chen, BC
Zhou, P
[J]. TETRAHEDRON, 1998, 54 (35) : 10481 - 10492
[38] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES
DAVIS, FA
CHEN, BC
[J]. CHEMICAL REVIEWS, 1992, 92 (05) : 919 - 934
[39] 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
[40] APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS
DAVIS, FA
SHEPPARD, AC
[J]. TETRAHEDRON, 1989, 45 (18) : 5703 - 5742

← 1 2 3 4 5 6 7 8 →