SULFUR(IV) COMPOUNDS AS LIGANDS .21. OXIDATION OF METAL-COORDINATED THIOETHERS WITH DIMETHYLDIOXIRANE - A NEW STEREOSELECTIVE SYNTHESIS OF CHIRAL SULFOXIDES

被引：54

作者：

SCHENK, WA ^{[1
]}

FRISCH, J ^{[1
]}

ADAM, W ^{[1
]}

PRECHTL, F ^{[1
]}

机构：

[1] UNIV WURZBURG,INST ORGAN CHEM,D-97074 WURZBURG,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 15-16期

关键词：

D O I：

10.1002/anie.199416091

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel variant of the asymmetric oxidation of prochiral thioethers yields chiral sulfoxides with selectivities of up to 98% de. The thioether is first coordinated to an enantiomerically pure auxiliary and then oxidized in the coordination sphere with dimethyldioxirane [Eq. (a)]. Smooth decomplexation is achieved with Nal. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1609 / 1611

页数：3

共 30 条

[1] THE STEREODYNAMICS OF METAL-COMPLEXES OF SULFUR-CONTAINING, SELENIUM-CONTAINING, AND TELLURIUM-CONTAINING LIGANDS [J].

ABEL, EW ;

BHARGAVA, SK ;

ORRELL, KG .

PROGRESS IN INORGANIC CHEMISTRY, 1984, 32 :1-118

[2] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[3] SYNTHESIS AND REACTIVITY OF SILICON-TRANSITION METAL-COMPLEXES .24. CONVERSION OF FERRIOSILANES TO FERRIOSILANOLS BY SELECTIVE OXIDATION OF THE SIH FUNCTION BY DIMETHYLDIOXIRANE [J].

ADAM, W ;

AZZENA, U ;

PRECHTL, F ;

HINDAHL, K ;

MALISCH, W .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (06) :1409-1411

[4] S(N)2 REACTION VERSUS ELECTRON-TRANSFER IN THE OXYGEN-TRANSFER BY DIMETHYLDIOXIRANE TO NITROGEN HETEROARENES [J].

ADAM, W ;

GOLSCH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (05) :737-739

[5]

ADAM W, 1993, ANGEW CHEM, V105, P771

[6] POSITIVELY CHARGED LIGANDS - THE SYNTHESIS, STRUCTURE, AND BONDING OF SULFONIUM ION COMPLEXES OF TRANSITION-METALS AND EVIDENCE FOR A METAL-INDUCED ACCELERATION OF THEIR DEALKYLATION [J].

ADAMS, RD ;

BLANKENSHIP, C ;

SEGMULLER, BE ;

SHIRALIAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4319-4326

[7] POSITIVELY CHARGED LIGANDS - COORDINATION BEHAVIOR OF SULFONIUM CATIONS [J].

ADAMS, RD ;

CHODOSH, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (03) :812-817

[8]

Andersen K. K., 1988, CHEM SULPHONES SULPH, p[823, 55]

[9]

ANDERSEN KK, 1984, J ORG CHEM, V49, P4070, DOI 10.1021/jo00195a042

[10] RULES GOVERNING ASYMMETRIC-SYNTHESIS WITH ORGANOTRANSITION METAL-COMPLEXES [J].

DAVIES, SG ;

SEEMAN, JI .

TETRAHEDRON LETTERS, 1984, 25 (17) :1845-1848

← 1 2 3 →