A NOVEL DISPLACEMENT ROUTE TO P-CHIRAL PHOSPHINE OXIDES OF HIGH ENANTIOMERIC PURITY

被引：16

作者：

CARDELLICCHIO, C

FIANDANESE, V

NASO, F

PACIFICO, S

KOPROWSKI, M

PIETRUSIEWICZ, KM

机构：

[1] UNIV BARI,DIPARTMENTO CHIM,CTR STUDIO METODOL INNOVAT SINTESI ORGAN,CNR,I-70126 BARI,ITALY

[2] POLISH ACAD SCI,CTR MOLEC & MACROMOLEC STUDIES,PL-90363 LODZ,POLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)73428-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of (R)-(1-chlorovinyl)methylphenylphosphine oxide with aryl and alkenyl Grignard reagents result in highly stereoselective displacement of the halovinyl group and afford virtually enantiomerically pure arylmethylphenyl and alkenylmethylphenylphosphine oxides of inverted configuration at phosphorus.

引用

收藏

页码：6343 / 6346

页数：4

相关论文

共 30 条

[1] EFFECT OF STRUCTURE ON RATE OF PYRAMIDAL INVERSION OF ACYCLIC PHOSPHINES [J].

BAECHLER, RD ;

MISLOW, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3090-&

[2] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF DIASTEREOMERIC MENTHYL BENZYLPHOSPHINATES [J].

BODALSKI, R ;

KOSZUK, J .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 44 (1-2) :99-102

[3] THE NUCLEOPHILIC DISPLACEMENT ROUTE TO HOMOCHIRAL ARYLPHOSPHINE OXIDES [J].

BROWN, JM ;

CAREY, JV ;

RUSSELL, MJH .

TETRAHEDRON, 1990, 46 (13-14) :4877-4886

[4] OPTICALLY-ACTIVE SULFOXIDES BY ENANTIOSPECIFIC REACTIONS OF BROMOVINYL ARYL SULFOXIDES WITH GRIGNARD-REAGENTS [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F ;

SCILIMATI, A .

TETRAHEDRON LETTERS, 1992, 33 (35) :5121-5124

[5] REACTIONS OF 2-HALOVINYL ARYL SULFOXIDES WITH ORGANOMETALLIC REAGENTS [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1718-1722

[6] REACTIONS OF (1-CHLOROVINYL)DIPHENYLPHOSPHINE OXIDE WITH ORGANOMETALLIC REAGENTS [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F ;

PIETRUSIEWICZ, KM ;

WISNIEWSKI, W .

TETRAHEDRON LETTERS, 1993, 34 (19) :3135-3138

[7] PREPARATION OF ENANTIOMERICALLY PURE PHOSPHINE OXIDES BY NUCLEOPHILIC DISPLACEMENT CHEMISTRY USING OXAZAPHOSPHOLIDINES [J].

CAREY, JV ;

BARKER, MD ;

BROWN, JM ;

RUSSELL, MJH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (07) :831-839

[8] USE OF CARBOHYDRATE-DERIVATIVES FOR STUDIES OF PHOSPHORUS STEREOCHEMISTRY .1. STEREOCHEMISTRY OF 1,3,2-DIOXAPHOSPHORINAN-2-ONES AND SYNTHESIS OF OPTICALLY-ACTIVE PHOSPHINE OXIDES [J].

COOPER, DB ;

INCH, TD ;

LEWIS, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (10) :1043-1048

[9] A NEW AND HIGHLY ENANTIOSELECTIVE SYNTHETIC ROUTE TO P-CHIRAL PHOSPHINES AND DIPHOSPHINES [J].

COREY, EJ ;

CHEN, ZL ;

TANOURY, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11000-11001

[10] A SIMPLE CHIRAL SHIFT-REAGENT FOR MEASUREMENT OF ENANTIOMERIC EXCESSES OF PHOSPHINE OXIDES [J].

DUNACH, E ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1985, 26 (22) :2649-2652