ENANTIOSELECTIVE SYNTHESIS OF THIOLS BY THIONE-THIOL REARRANGEMENT CATALYZED BY OPTICALLY-ACTIVE PYRIDINE N-OXIDES

被引：27

作者：

DIANA, MB

MARCHETTI, M

MELLONI, G

机构：

[1] CNR,IST APPLICAZ TECN CHIM AVANZATE PROBLEMI AGRO,I-07100 SASSARI,ITALY

[2] UNIV SASSARI,DIPARTIMENTO CHIM,I-07100 SASSARI,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期

关键词：

D O I：

10.1016/0957-4166(95)00143-D

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically enriched thiols were prepared by rearrangement under mild conditions of racemic carbonodithioic O,S-dialkyl esters catalyzed by optically active pyridine N-oxides, followed by reaction with 2-aminoethanol of the carbonodithioic S,S-dialkyl esters thus formed. Enantioselectivities up to 37.7% was obtained.

引用

收藏

页码：1175 / 1179

页数：5

相关论文

共 30 条

[1] A CONVENIENT ACCESS TO CHIRAL SULFONIC-ACIDS [J].

AGAMI, C ;

PRINCE, B ;

PUCHOT, C .

SYNTHETIC COMMUNICATIONS, 1990, 20 (21) :3289-3294

[2]

AZZENA U, 1986, GAZZ CHIM ITAL, V116, P307

[3]

BERETTA E, 1974, SYNTHESIS-STUTTGART, P425

[4]

BLANCO JM, 1990, SYNTHESIS-STUTTGART, P584

[5] OPTICALLY-ACTIVE NITROGEN LIGANDS .3. ENANTIOFACE-DISCRIMINATING TRANSFER HYDROGENATION OF ACETOPHENONE CATALYZED BY RHODIUM(I) COMPLEXES WITH CHIRAL 2-(2'-PYRIDYL)PYRIDINES [J].

BOTTEGHI, C ;

CHELUCCI, G ;

CHESSA, G ;

DELOGU, G ;

GLADIALI, S ;

SOCCOLINI, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 304 (1-2) :217-225

[6] ASYMMETRIC CATALYSIS .46. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 AND OPTICALLY-ACTIVE NITROGEN LIGANDS [J].

BOTTEGHI, C ;

SCHIONATO, A ;

CHELUCCI, G ;

BRUNNER, H ;

KURZINGER, A ;

OBERMANN, U .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :17-31

[7] STEREOCHEMISTRY OF OXIDATION OF NICOTINE TO ITS 1'-N-OXIDES - ACTION OF TUNGSTATE (VI) AND MOLYBDATE (VI) [J].

BRANDANGE, S ;

LINDBLOM, L ;

SAMUELSSON, D .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1977, 31 (10) :907-909

[8]

CHIELLINI E, 1971, INT J SULFUR CHEM A, V1, P73

[9] AN IMPROVED PREPARATION OF TERTIARY AMINE N-OXIDES [J].

CRAIG, JC ;

PURUSHOT.KK .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1721-&

[10]

DEGANI I, 1980, SYNTHESIS-STUTTGART, P375