SELECTIVE OXIDATION OF OPTICALLY-ACTIVE SEC,SEC-1,2-DIOLS BY DIOXIRANES - A PRACTICAL METHOD FOR THE SYNTHESIS OF HOMOCHIRAL ALPHA-HYDROXY KETONES IN HIGH OPTICAL PURITY

被引：49

作者：

D'ACCOLTI, L ^{[1
]}

DETOMASO, A ^{[1
]}

FUSCO, C ^{[1
]}

ROSA, A ^{[1
]}

CURCI, R ^{[1
]}

机构：

[1] UNIV BARI, CNR, CTR MISO, DEPT CHEM, V AMENDOLA 173, I-70126 BARI, ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 14期

关键词：

D O I：

10.1021/jo00066a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By employing either dimethyldioxirane or its trifluoromethyl analog, the direct, high-yield conversion of one cyclic and three open chain optically sec,sec-1,2-diols to the corresponding alpha-hydroxy ketones in high optical yield has been achieved.

引用

页码：3600 / 3601

页数：2

共 48 条

[1]

AAMBONI R, 1986, HELV CHIM ACTA, V69, P615

[2] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[3] THIANTHRENE 5-OXIDE AS A MECHANISTIC PROBE FOR ASSESSING THE ELECTRONIC CHARACTER OF OXYGEN-TRANSFER AGENTS [J].

ADAM, W ;

HAAS, W ;

LOHRAY, BB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6202-6208

[4]

ADAM W, 1993, TOP CURR CHEM, V164, P45

[5]

Adam W., 1992, ORGANIC PEROXIDES, P195

[6]

AUDIER HE, 1966, B SOC CHIM FR, P2811

[7] ALUMINUM-HYDRIDE REDUCTION OF ALPHA-KETOLS .2. ADDITIONAL EVIDENCE FOR CONFORMATIONAL FLEXIBILITY IN TRANSITION-STATE [J].

BOWLUS, SB ;

KATZENEL.JA .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3309-3314

[8] THE CONFIGURATION OF ATROLACTIC ACID - RETENTION OF CONFIGURATION IN THE ACID-CATALYZED RING OPENING OF STILBENE OXIDES [J].

BREWSTER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :4061-4064

[9] O-17 AND C-13 IDENTIFICATION OF THE DIMETHYLDIOXIRANE INTERMEDIATE ARISING IN THE REACTION OF POTASSIUM CARBONATE WITH ACETONE [J].

CASSIDEI, L ;

FIORENTINO, M ;

MELLO, R ;

SCIACOVELLI, O ;

CURCI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :699-700

[10]

COREY EJ, 1974, TETRAHEDRON LETT, P287

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