SYNTHESIS OF FLUORINATED CHIRONS - STEREOSELECTIVE OXIRANE FORMATION BY REACTION OF DIAZOMETHANE ON 1-FLUORO-3-ARYLSULFINYL-2-PROPANONE AND RING-OPENING BY SELECTED NUCLEOPHILES

被引：13
作者：
ARNONE, A
BRAVO, P
FRIGERIO, M
SALANI, G
VIANI, F
ZAPPALA, C
CAVICCHIO, G
CRUCIANELLI, M
机构：
[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM,POLITECN,I-20133 MILAN,ITALY
[2] UNIV AQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67010 COPPITO,ITALY
来源：
TETRAHEDRON | 1995年 / 51卷 / 30期
关键词：
D O I：
10.1016/0040-4020(95)00430-G
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(R)-1-fluoro-3-[(4-methylphenyl)sulfinyl]-2-propanone (1) reacts with diazomethane affording (S)-2-(fluoromethyl)-2- {[(R)-(4-methylphenyl)sulfinyl]methyl}oxirane (2) as the main product. The influence of reaction conditions (solvent, temperature) on the chemo- and stereoselectivity has been studied. Several elaborations of 2, including reactions on the chiral auxiliary and opening of the oxirane ring by carbon, nitrogen oxygen, phosphorus and halogen nucleophiles, are described. Full structural elucidation of the products is provided
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页码：8289 / 8310
页数：22
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