LARGE-SCALE ASYMMETRIC-SYNTHESIS OF A BIOLOGICALLY-ACTIVE SULFOXIDE

被引：43

作者：

PITCHEN, P

FRANCE, CJ

MCFARLANE, IM

NEWTON, CG

THOMPSON, DM

机构：

[1] Rhône-Poulenc Rorer Ltd., Dagenham Research Centre, Dagenham, Essex RM10 7XS, Rainham Road South

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 03期

关键词：

ASYMMETRIC SULFOXIDATION; OPTICALLY PURE SULFOXIDES; MODIFIED SHARPLESS REAGENT;

D O I：

10.1016/0040-4039(94)85087-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of sulfoxide RP 73163 is described. The synthetic strategy is based on the enantioselective oxidation of a suitably designed prochiral methyl sulfide, followed by a alkylation of the resulting sulfoxide.

引用

页码：485 / 488

页数：4

共 17 条

[1] RP-70676 - A POTENT SYSTEMICALLY AVAILABLE INHIBITOR OF ACYL-COA-CHOLESTEROL O-ACYL TRANSFERASE (ACAT) [J].

ASHTON, MJ ;

BRIDGE, AW ;

BUSH, RC ;

DRON, DI ;

HARRIS, NV ;

JONES, GD ;

LYTHGOE, DJ ;

RIDDELL, D ;

SMITH, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (05) :375-380

[2] STEREOCHEMISTRY OF INTRAMOLECULAR HOMOLYTIC SUBSTITUTION AT THE SULFUR ATOM OF A CHIRAL SULFOXIDE [J].

BECKWITH, ALJ ;

BOATE, DR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (03) :189-190

[3] TARTRATE-LIKE LIGANDS IN THE ASYMMETRIC EPOXIDATION [J].

BURNS, CJ ;

MARTIN, CA ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2826-2834

[4] ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRIDINE SULFONES [J].

DAVIS, R ;

KERN, JR ;

KURZ, LJ ;

PFISTER, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7873-7874

[5]

DIFURIA F, 1984, SYNTHESIS-STUTTGART, P325

[6] A MECHANISTIC APPROACH TO THE ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS AND OSMYLATION OF ALKENES [J].

JORGENSEN, KA .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :515-532

[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[8] THE ENANTIOSELECTIVE SYNTHESIS OF (-)-PHYSOSTIGMINE VIA CHIRAL SULFOXIDES [J].

MARINO, JP ;

BOGDAN, S ;

KIMURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5566-5572

[9] KINETIC RESOLUTION OF A RACEMIC SULFIDE BY ENANTIOSELECTIVE SULFOXIDE FORMATION [J].

PHILLIPS, ML ;

BERRY, DM ;

PANETTA, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :4047-4049

[10] AN EFFICIENT ASYMMETRIC OXIDATION OF SULFIDES TO SULFOXIDES [J].

PITCHEN, P ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1984, 25 (10) :1049-1052

← 1 2 →