Synthesis and reactions of enantiomerically pure chloromethyl oxiranes

被引：6

作者：

Abrate, F ^{[1
]}

Bravo, P ^{[1
]}

Frigerio, M ^{[1
]}

Viani, F ^{[1
]}

Zanda, M ^{[1
]}

机构：

[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20131 MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 02期

关键词：

D O I：

10.1016/0957-4166(96)00042-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reactivities of 1-chloro-3-p-tolylsufinyl acetone (RS)-1 towards diazomethane and of the resulting diastereoisomeric 1-chloromethyl-1-sulfinylmethyl oxiranes 2 towards O-, N- and C-centred nucleophiles are investigated. The synthesis of differently functionalized homochiral chlorinated sulphur-free oxiranes (R)-15, (S)-16 and (R)-17 has been accomplished in good chemical yields.

引用

页码：581 / 594

页数：14

共 49 条

[1] ARNDT F, 1928, CHEM BER, V61, P65
[2] SYNTHESIS OF FLUORINATED CHIRONS - STEREOSELECTIVE OXIRANE FORMATION BY REACTION OF DIAZOMETHANE ON 1-FLUORO-3-ARYLSULFINYL-2-PROPANONE AND RING-OPENING BY SELECTED NUCLEOPHILES
ARNONE, A
BRAVO, P
FRIGERIO, M
SALANI, G
VIANI, F
ZAPPALA, C
CAVICCHIO, G
CRUCIANELLI, M
[J]. TETRAHEDRON, 1995, 51 (30) : 8289 - 8310
[3] SYNTHETICALLY USEFUL C-4 FLUORINATED BUILDING-BLOCKS BEARING A QUATERNARY STEREOCENTER
ARNONE, A
BRAVO, P
FRIGERIO, M
SALANI, G
VIANI, F
[J]. TETRAHEDRON, 1994, 50 (47) : 13485 - 13492
[4] ARNONE A, 1995, IN PRESS TETRAHEDRON
[5] BARTOK M, 1985, SMALL RING HETEROC 3
[6] ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE 4'-FLUOROALKYL-2',3'-DIDEOXY NUCLEOSIDES
BRAVO, P
MELE, A
SALANI, G
VIANI, F
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (13) : 1577 - 1580
[7] SYNTHESIS OF OPTICALLY PURE "ALPHA-HALO-ALPHA'-SULPHINYL-KETONES
BRAVO, P
RESNATI, G
[J]. TETRAHEDRON LETTERS, 1985, 26 (45) : 5601 - 5604
[8] BRAVO P, 1989, J CHEM RES-S, P134
[9] OPTICALLY PURE AND FLUORO SUBSTITUTED CARBOACYCLIC NUCLEOSIDE ANALOGS
BRAVO, P
FRIGERIO, M
SOLOSHONOK, V
VIANI, F
[J]. TETRAHEDRON LETTERS, 1993, 34 (48) : 7771 - 7772
[10] HOMOCHIRAL FLUORO-ORGANIC COMPOUNDS .12. ALPHA-HYDROXY BETA-FLUORO ALDEHYDES AND ESTERS, FLUORO EPOXIDES AND GLYCOLS FROM FLUORINATED SULFINYL CHIRONS
BRAVO, P
PIOVOSI, E
RESNATI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07): : 1201 - 1208

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