Scandium(III) triflate as an efficient and recyclable catalyst for chemoselective conversion of carbonyl compounds to 1,3-oxathiolanes

被引：26

作者：

Karimi, B ^{[1
]}

Ma'mani, L ^{[1
]}

机构：

[1] IASBS, Dept Chem, Gava Zang, Zanjan, Iran

来源：

SYNTHESIS-STUTTGART | 2003年 / 16期

关键词：

heterocycles; protecting groups; acetals; scandium; aldehydes; ketones; catalysis;

D O I：

10.1055/s-2003-42436

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of carbonyl compounds can be easily and rapidly converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of scandium(III) triflate [Sc(OTf)(3)] in CH2Cl2. After completion of the reaction, the catalyst can straightforwardly be recovered using standard methods. Moreover, by employing this protocol, chemoselective oxathioacetalization of aldehydes in the presence of ketones can be achieved.

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页码：2503 / 2506

页数：4

相关论文

共 32 条

[1] ORGANIC SULFUR-COMPOUNDS .2. SULFUR-DIOXIDE AS CATALYST IN THE SYNTHESIS OF THIOACETALS FROM ALDEHYDES OR KETONES AND ALKANETHIOLS, ALKANEDITHIOLS, OR HYDROXYALKANETHIOLS [J].

BURCZYK, B ;

KORTYLEWICZ, Z .

SYNTHESIS-STUTTGART, 1982, (10) :831-833

[2] Metal salt-catalyzed addition of lithium enolates of ketones to 1,2-epoxides, an efficient route to alpha-alkyl-gamma-hydroxy ketones [J].

Crotti, P ;

DiBussolo, V ;

Favero, L ;

Pineschi, M ;

Pasero, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9548-9552

[3] STUDIES IN ORGANIC SULFUR COMPOUNDS .6. CYCLIC ETHYLENE AND TRIMETHYLENE HEMITHIOKETALS [J].

DJERASSI, C ;

GORMAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3704-3708

[4] HIGHLY STEREOSELECTIVE ASYMMETRIC-SYNTHESIS OF (R)-(-)-MEVALOLACTONE [J].

ELIEL, EL ;

SOAI, K .

TETRAHEDRON LETTERS, 1981, 22 (30) :2859-2862

[5] REDUCTIONS WITH METAL HYDRIDES .13. HYDROGENOLYSIS OF HEMITHIOACETALS AND HEMITHIOKETALS WITH LITHIUM ALUMINUM HYDRIDE-ALUMINUM CHLORIDE [J].

ELIEL, EL ;

PILATO, LA ;

BADDING, VG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (12) :2377-&

[6] ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .1. SCOPE OF THE REACTION [J].

ELIEL, EL ;

MORRISNATSCHKE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2937-2942

[7] ASYMMETRIC-SYNTHESIS OF (R)-CITRAMALATE AND (S)-CITRAMALATE IN HIGH ENANTIOMERIC PURITY [J].

FRYE, SV ;

ELIEL, EL .

TETRAHEDRON LETTERS, 1985, 26 (33) :3907-3910

[8] CHEMISTRY OF 1,3-OXATHIANES - SYNTHESIS AND CONFORMATION OF 2-SUBSTITUTED 1,3-OXATHIANES [J].

FUJI, K ;

UEDA, M ;

SUMI, K ;

KAJIWARA, K ;

FUJITA, E ;

IWASHITA, T ;

MIURA, I .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :657-661

[9] SYNTHESIS OF 2-HETEROSUBSTITUTED 1,3-OXATHIANES AND THEIR REACTION WITH SEC-BUTYLLITHIUM [J].

FUJI, K ;

UEDA, M ;

SUMI, K ;

FUJITA, E .

TETRAHEDRON LETTERS, 1981, 22 (21) :2005-2008

[10] 2-LITHIO-2-TRIMETHYLSILYL-1,3-OXATHIAN - A POSSIBLE ACYL DIANION EQUIVALENT [J].

FUJI, K ;

UEDA, M ;

FUJITA, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (01) :49-50

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