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

[1] HIGHLY EFFICIENT HYDROXYLATION OF CARBONYL-COMPOUNDS WITH DIMETHYLDIOXIRANE
ADAM, W
PRECHTL, F
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2369 - 2372
[2] Nickel-catalyzed hydroxylation of 1,3-dicarbonyl compounds by dimethyldioxirane
Adam, W
Smerz, AK
[J]. TETRAHEDRON, 1996, 52 (16) : 5799 - 5804
[3] ADAM W, 1993, TOP CURR CHEM, V164, P45
[4] Adam W., 2004, ORG REACTIONS, V61, P219, DOI DOI 10.1039/C3SC52649F
[5] A new approach to the synthesis of long-chain polypropionates based on the Diels-Alder monoadditions of 2,2'-ethylidenebis[3,5-dimethylfuran]
Ancerewicz, J
Vogel, P
[J]. HELVETICA CHIMICA ACTA, 1996, 79 (05) : 1393 - 1414
[6] ANDERSON JC, 1990, SYNLETT, P107
[7] Regioselective Dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives
Andrews, MD
Brewster, AG
Crapnell, KM
Ibbett, AJ
Jones, T
Moloney, MG
Prout, K
Watkin, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02): : 223 - 235
[8] A NEW EFFICIENT TOTAL SYNTHESIS OF VINDOROSINE AND VINDOLINE
ANDRIAMIALISOA, RZ
LANGLOIS, N
LANGLOIS, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) : 961 - 967
[9] ALPHA-HYDROXYLATION OF BETA-DICARBONYL COMPOUNDS
ANDRIAMIALISOA, RZ
LANGLOIS, N
LANGLOIS, Y
[J]. TETRAHEDRON LETTERS, 1985, 26 (30) : 3563 - 3566
[10] [Anonymous], ORG SYNTH COLL

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