DIRECT ALPHA-HYDROXYLATION OF KETONES UNDER ACIDIC CONDITIONS USING [BIS (TRIFLUOROACETOXY)] IODOBENZENE

被引：92

作者：

MORIARTY, RM

BERGLUND, BA

PENMASTA, R

机构：

[1] Department of Chemistry, University of Illinois at Chicago, Chicago

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)60007-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Bis(trifluoroacetoxy)] iodobenzene and trifluoroacetic acid in CH3CN/H2O reacts with aromatic, heteroaromatic, and aliphatic ketones to afford alpha-hydroxyketones in moderate to good yields.

引用

页码：6065 / 6068

页数：4

共 49 条

[1] HIGHLY EFFICIENT HYDROXYLATION OF CARBONYL-COMPOUNDS WITH DIMETHYLDIOXIRANE [J].

ADAM, W ;

PRECHTL, F .

CHEMISCHE BERICHTE, 1991, 124 (10) :2369-2372

[2] VETISPIRANE SESQUITERPENE GLUCOSIDES FROM FLUE-CURED VIRGINIA TOBACCO - STRUCTURE, ABSOLUTE STEREOCHEMISTRY, AND SYNTHESIS - X-RAY STRUCTURE OF PARA-BROMOBENZENESULFONATE OF ONE OF DERIVED AGLYCONES [J].

ANDERSON, RC ;

GUNN, DM ;

MURRAYRUST, J ;

MURRAYRUST, P ;

ROBERTS, JS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (01) :27-28

[3] COMPOUNDS RELATED TO STEROID HORMONES .9. OXYGENATION OF STEROID KETONES IN STRONGLY BASIC MEDIUM - NEW METHOD OF PREPARATION OF 17ALPHA-HYDROXYPREGNAN-20-ONES [J].

BAILEY, EJ ;

TEMPLETON, JF ;

ELKS, J ;

BARTON, DHR .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAY) :1578-&

[4] SYNTHETIC STUDIES DIRECTED TOWARD THE NATURALLY-OCCURRING ACYL TETRAMIC ACIDS .1. CONVERGENT TOTAL SYNTHESIS OF (+/-)-TIRANDAMYCIN-A [J].

BOECKMAN, RK ;

STARRETT, JE ;

NICKELL, DG ;

SUM, PE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5549-5559

[5] 1,4-SILYL REARRANGEMENTS OF SILOXYALKENES TO SILOXY-KETONES DURING PEROXIDATION [J].

BROOK, AG ;

MACRAE, DM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 77 (02) :C19-C21

[6]

BUCHI G, 1968, J AM CHEM SOC, V90, P2448

[7]

CAIN C, 1987, TETRAHEDRON LETT, P3723

[8] OXIDATION OF SILYL ENOL ETHERS USING 2-SULFONYLOXAZIRIDINES - SYNTHESIS OF ALPHA-SILOXY EPOXIDES AND ALPHA-HYDROXY CARBONYL-COMPOUNDS [J].

DAVIS, FA ;

SHEPPARD, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :954-955

[9] ENANTIOSELECTIVE SYNTHESIS OF TERTIARY ALPHA-HYDROXY CARBONYL-COMPOUNDS USING ((8,8-DICHLOROCAMPHORYL)SULFONYL)OXAZIRIDINE [J].

DAVIS, FA ;

WEISMILLER, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3715-3717

[10] SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

VISHWAKARMA, LC ;

BILLMERS, JM ;

FINN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3241-3243

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