DEPENDENCE OF THE ENANTIOSELECTIVITY ON THE NATURE OF THE BASE IN A HORNER-WADSWORTH-EMMONS REACTION LEADING TO VINYL SULFOXIDES

被引：10

作者：

CARDELLICCHIO, C ^{[1
]}

IACUONE, A ^{[1
]}

NASO, F ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 36期

关键词：

D O I：

10.1016/0040-4039(95)01287-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselectivity of the HWE synthesis of chiral methyl (Z)- and (E)-3-p-tolylsulfinylpropenoate was found to depend upon the nature of the base, the e.e. values being in the range 5-->98%.

引用

页码：6563 / 6566

页数：4

共 17 条

[1] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[2] 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

[3] A NOVEL DISPLACEMENT ROUTE TO P-CHIRAL PHOSPHINE OXIDES OF HIGH ENANTIOMERIC PURITY [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F ;

PACIFICO, S ;

KOPROWSKI, M ;

PIETRUSIEWICZ, KM .

TETRAHEDRON LETTERS, 1994, 35 (34) :6343-6346

[4] 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

[5] 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

[6] AN EFFICIENT BIOCATALYZED KINETIC RESOLUTION OF METHYL (Z)-3-ARYLSULPHINYLPROPENOATES [J].

CARDELLICCHIO, C ;

NASO, F ;

SCILIMATI, A .

TETRAHEDRON LETTERS, 1994, 35 (26) :4635-4638

[7] ENANTIOMERIC ENRICHMENT OF SULFOXIDES BY PREPARATIVE FLASH CHROMATOGRAPHY ON AN ACHIRAL PHASE [J].

DITER, P ;

TAUDIEN, S ;

SAMUEL, O ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :370-373

[8]

DRABOWICZ J, 1988, CHEM SULPHONES SULPH, P233

[9]

GUESSOUS AR, 1988, B SOC CHIM FR, P727

[10]

HEATHCOCK CH, 1987, HETEROCYCLES, V25, P75

← 1 2 →