A NEW STEREOSELECTIVE SYNTHESIS OF CHIRAL TETRAHYDROTHIOPYRANS AND THEIR CORRESPONDING SULFOXIDES

被引:25
作者
HACHEM, A
TOUPET, L
GREE, R
机构
[1] ECOLE NATL SUPER CHIM RENNES,CNRS,SYNTH & ACTIVAT BIOMOLEC LAB,F-35700 RENNES,FRANCE
[2] UNIV RENNES,CNRS,MAT CONDENSEE & MAT GRP,F-35042 RENNES,FRANCE
关键词
D O I
10.1016/0040-4039(95)00139-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new stereoselective synthesis of chiral tetrahydrothiopyrans as been achieved based upon the intramolecular trapping of pentadienyl cations complexed to Fe(CO)(3) By sulfur nucleophiles. Oxidation of these heterocycles with Oxone(R) is compatible,with the organometallic moiety and leads in good diastereoselectivity to the corresponding sulfoxides.
引用
收藏
页码:1849 / 1852
页数:4
相关论文
共 26 条
[1]   CHEMOSELECTIVE METHYLTRIOXORHENIUM(VII)-CATALYZED SULFOXIDATIONS WITH HYDROGEN-PEROXIDE [J].
ADAM, W ;
MITCHELL, CM ;
SAHAMOLLER, CR .
TETRAHEDRON, 1994, 50 (46) :13121-13124
[2]  
BOWER JF, 1994, TETRAHEDRON LETT, P7111
[3]   CONFORMATIONAL ANALYSIS OF TRICARBONYL(DIENE)IRON COMPOUNDS [J].
CLINTON, NA ;
LILLYA, CP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3058-&
[4]  
DIFURIA F, 1984, SYNTHESIS-STUTTGART, P325
[5]   HIGHLY ENANTIOSELECTIVE OXIDATION OF FERROCENYL SULFIDES [J].
DITER, P ;
SAMUEL, O ;
TAUDIEN, S ;
KAGAN, HB .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :549-552
[6]   ACID-CATALYZED CYCLIZATION OF 1,4-DIOLS TETHERED TO (BUTADIENE)IRON TRICARBONYL SEGMENTS - ISOTOPIC LABELING AS A MECHANISTIC PROBE OF STEREOCHEMICAL RETENTION DURING TETRAHYDROFURAN FORMATION [J].
GREE, D ;
GREE, R ;
LOWINGER, TB ;
MARTELLI, J ;
NEGRI, JT ;
PAQUETTE, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8841-8846
[7]  
GREE D, UNPUB
[8]   ACYCLIC BUTADIENE IRON TRICARBONYL COMPLEXES IN ORGANIC-SYNTHESIS [J].
GREE, R .
SYNTHESIS-STUTTGART, 1989, (05) :341-355
[9]  
GREE R, IN PRESS ADV METAL O, V4
[10]   SULFOXIDES AND STEREOCHEMICAL CONTROL IN ORGANOMETALLIC CHEMISTRY [J].
GRIFFITHS, SL ;
MARCOS, CF ;
PERRIO, S ;
SABERI, SP ;
THOMAS, SE ;
TUSTIN, GJ ;
WIERZCHLEYSKI, AT .
PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1565-1572