Stereospecific synthesis of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole using aryl diphenylphosphinite and azide compounds by a new type of oxidation-reduction condensation

被引:8
作者
Kuroda, Kiichi [1 ]
Maruyama, Yuji [2 ]
Hayashi, Yujiro [1 ]
Mukaiyama, Teruaki [3 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
[3] Kitasato Univ, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
关键词
D O I
10.1246/cl.2008.836
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The preparation of alkyl aryl Sulfides front alcohols and 2-sulfanylbenzothiazole using phenyl diphenylphosphinite and azide compounds by a new type of oxidation-reduction condensation is described. The chiral secondary and tertiary alcohols are converted into the corresponding chiral Sulfides with almost complete inversion of configurations under mild and neutral conditions.
引用
收藏
页码:836 / 837
页数:2
相关论文
共 17 条
[1]   An efficient method for the preparation of monoalkylated sulfonamides from unsubstituted sulfonamides and alkyl diphenylphosphinites by oxidation-reduction condensation using trimethylsilylmethyl azide [J].
Aoki, H ;
Kuroda, K ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (09) :1266-1267
[2]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[3]   Recent progress in the synthesis of heterocyclic natural products by the Staudinger/intramolecular aza-Wittig reaction [J].
Eguchi, S .
ARKIVOC, 2005, :98-119
[4]   Application of iminophosphorane-based methodologies for the synthesis of natural products [J].
Fresneda, PM ;
Molina, P .
SYNLETT, 2004, (01) :1-17
[5]   RECENT ADVANCES IN THE STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
KASUKHIN, LF .
TETRAHEDRON, 1992, 48 (08) :1353-1406
[6]   Stereospecific C-S bond formation from chiral tertiary alcohols by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites and its application to the synthesis of a chiral tertiary thiol [J].
Ikegai, Kazuhiro ;
Pluempanupat, Wanchai ;
Mukaiyama, Teruaki .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (05) :780-790
[7]   The Staudinger ligation -: A gift to chemical biology' [J].
Köhn, M ;
Breinbauer, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) :3106-3116
[8]   Preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole by a new type of oxidation-reduction condensation using aryl diphenylphosphinite and benzoquinone derivatives [J].
Kuroda, Kiichi ;
Hayashi, Yujiro ;
Mukaiyama, Teruaki .
CHEMISTRY LETTERS, 2008, 37 (06) :592-593
[9]  
MOLINA P, 1994, SYNTHESIS-STUTTGART, P1197
[10]   A new method for the preparation of nitrogen-containing cyclic compounds from p-nitrobenzenesulfonamide and alkyl bis(diphenylphosphinite)s by oxidation-reduction condensation using 1-azidoadamantane [J].
Mukaiyama, T ;
Kuroda, K ;
Aoki, H .
CHEMISTRY LETTERS, 2005, 34 (12) :1644-1645