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
收藏
页码：581 / 594
页数：14
相关论文
共 50 条
  • [1] Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines
    Hachiya, S
    Cook, AS
    Williams, DBG
    Montalban, AG
    Barrett, AGM
    Hoffman, BM
    TETRAHEDRON, 2000, 56 (35) : 6565 - 6569
  • [2] Synthesis and reactivity of enantiomerically pure 2-fluoromethyl-2-(1′-p-tolylsulfinyl)alkyl oxiranes
    Arnone, A
    Bravo, P
    Frigerio, M
    Viani, F
    Soloshonok, VA
    TETRAHEDRON, 1998, 54 (39) : 11825 - 11840
  • [3] Synthesis of enantiomerically pure anthracyclinones
    Achmatowicz, Osman
    Szechner, Barbara
    ANTHRACYCLINE CHEMISTRY AND BIOLOGY I: BIOLOGICAL OCCURENCE AND BIOSYNTHESIS, SYNTHESIS AND CHEMISTRY: BIOLOGICAL OCCURENCE AND BIOSYNTHESIS, SYNTHESIS AND CHEMISTRY, 2008, 282 : 143 - 186
  • [4] Synthesis of enantiomerically pure cyclohexylglycine
    Minnaard, AJ
    Boesten, WHJ
    Zeegers, HJM
    SYNTHETIC COMMUNICATIONS, 1999, 29 (24) : 4327 - 4332
  • [5] SYNTHESIS OF AN ENANTIOMERICALLY PURE INDOLOSESQUITERPENE
    SARRAGIOTTO, MH
    GOWER, AE
    MARSAIOLI, AJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03): : 559 - 562
  • [6] CYCLITOL REACTIONS .5. SYNTHESIS OF ENANTIOMERICALLY PURE VALIENAMINE FROM QUEBRACHITOL
    PAULSEN, H
    HEIKER, FR
    LIEBIGS ANNALEN DER CHEMIE, 1981, (12): : 2180 - 2203
  • [7] Synthesis of allylamines in enantiomerically pure form
    Concellón, JM
    Baragaña, B
    Riego, E
    TETRAHEDRON LETTERS, 2000, 41 (22) : 4361 - 4362
  • [8] Synthesis of enantiomerically pure δ-benzylproline derivatives
    Rodriguez, Isabel
    Isabel Calaza, M.
    Jimenez, Ana I.
    Cativiela, Carlos
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (05) : 3310 - 3318
  • [9] SYNTHESIS OF ENANTIOMERICALLY PURE LYSOPHOSPHATIDYLINOSITOLS AND ALKYLPHOSPHOINOSITOLS
    FILTHUTH, E
    EIBL, H
    CHEMISTRY AND PHYSICS OF LIPIDS, 1992, 60 (03) : 253 - 261
  • [10] Total Synthesis of Enantiomerically Pure (-)-Balanol
    Chimia Chemie Rep, 11 (530):
12345