A remarkable iodine-catalyzed protection of carbonyl compounds

被引：70

作者：

Banik, BK ^{[1
]}

Chapa, M ^{[1
]}

Marquez, J ^{[1
]}

Cardona, M ^{[1
]}

机构：

[1] Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 13期

关键词：

D O I：

10.1016/j.tetlet.2005.01.176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here a remarkably simple molecular iodine-catalyzed protection method for various carbonyl Compounds as ketals in a general reaction. The iodine-catalyzed reaction of mandelic acid and lactic acid with several aldehydes has furnished a highly diastereoselective synthesis of cis and trans dioxolanones. (c) 2005 Published by Elsevier Ltd.

引用

页码：2341 / 2343

页数：3

共 40 条

[11]

CHAN TH, 1983, SYNTHESIS-STUTTGART, P203

[12] A NEW HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF 2,5-DISUBSTITUTED-1,3-DIOXOLAN-4-ONES FROM ALPHA-HYDROXYACIDS [J].

CHAPEL, N ;

GREINER, A ;

ORTHOLAND, JY .

TETRAHEDRON LETTERS, 1991, 32 (11) :1441-1442

[13] Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride.: Facile synthesis of β-keto enol ethers [J].

Clerici, A ;

Pastori, N ;

Porta, O .

TETRAHEDRON, 2001, 57 (01) :217-225

[14] Efficient acetalisation of aldehydes catalyzed by titanium tetrachloride in a basic medium [J].

Clerici, A ;

Pastori, N ;

Porta, O .

TETRAHEDRON, 1998, 54 (51) :15679-15690

[15] ORGANIC-REACTIONS AT HIGH-PRESSURE - CONVERSION OF CYCLIC ALKANONES AND ENONES TO 1,3-DIOXOLANES [J].

DAUBEN, WG ;

GERDES, JM ;

LOOK, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4964-4970

[16] CHOLESTEROL AND COMPANIONS .9. OXIDATION OF DELTA-5-CHOLESTENE-3-ONE WITH LEAD TETRAACETATE [J].

FIESER, LF ;

STEVENSON, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) :1728-1733

[17] LANTHANOIDS IN ORGANIC-SYNTHESIS .4. SELECTIVE KETALIZATION AND REDUCTION OF CARBONYL GROUPS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4187-4189

[18] THE CHEMISTRY OF SOME 5-M-DITHIANONES AND DITHIACYCLOALKANONES [J].

HOWARD, EG ;

LINDSEY, RV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (01) :158-164

[19] 5-ALKYL-2-TERT-BUTYL-1,3-DIOXOLAN-4-ONES BY TRIMETHYLSILYL TRIFLATE CATALYZED-REACTIONS BETWEEN BIS(TRIMETHYLSILYL) DERIVATIVES OF ALPHA-HYDROXY CARBOXYLIC-ACIDS AND PIVALDEHYDE [J].

HOYE, TR ;

PETERSON, BH ;

MILLER, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1351-1353

[20]

Ishihara K, 1996, SYNLETT, P839

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