Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines

被引：54

作者：

Davis, FA ^{[1
]}

Liu, H

Chen, BC

Zhou, P

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] Drexel Univ, Dept Chem, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00500-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate alpha-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82-95%) were observed only for enolates of beta-ketoesters where the keto group is part of a 6-membered ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10481 / 10492

页数：12

共 43 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] TOTAL SYNTHESIS OF (+/-)-VINDOLINE
ANDO, M
BUCHI, G
OHNUMA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) : 6880 - 6881
[4] ALPHA-HYDROXYLATION OF BETA-DICARBONYL COMPOUNDS
ANDRIAMIALISOA, RZ
LANGLOIS, N
LANGLOIS, Y
[J]. TETRAHEDRON LETTERS, 1985, 26 (30) : 3563 - 3566
[5] A NEW ASPECT OF THE BAYER-VILLIGER OXIDATION OF 1,3-DICARBONYL COMPOUNDS
BIRD, CW
DOTSE, AK
[J]. TETRAHEDRON LETTERS, 1991, 32 (21) : 2413 - 2414
[6] EPOXIDATION WITH DIOXIRANES DERIVED FROM 2-FLUORO-2-SUBSTITUTED-1-TETRALONES AND 2-FLUORO-2-SUBSTITUTED-1-INDANONES
BROWN, DS
MARPLES, BA
SMITH, P
WALTON, L
[J]. TETRAHEDRON, 1995, 51 (12) : 3587 - 3606
[7] BUCHI G, 1971, J AM CHEM SOC, V93, P3299
[8] ENANTIOSELECTIVE SYNTHESIS OF (+)-KJELLMANIANONE
CHEN, BC
WEISMILLER, MC
DAVIS, FA
BOSCHELLI, D
EMPFIELD, JR
SMITH, AB
[J]. TETRAHEDRON, 1991, 47 (02) : 173 - 182
[9] CHEN BC, 1995, ORG SYNTH, V73, P98
[10] ACTIVE IN ALPHA-CHYMOTRYPSIN - METHYL 3,4-DIHYDROISOCOUMARIN-3-CARBOXYLATE 1
COHEN, SG
SCHULTZ, RM
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1967, 57 (02) : 243 - &

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