Highly enantiospecific oxyfunctionalization of nonactivated hydrocarbon sites by perfluoro-cis-2-n-butyl-3-n-propyloxaziridine

被引：17
作者：
Arnone, A
Folettto, S
Metrangolo, P
Pregnolato, M
Resnati, G
机构：
[1] Polytechn Milano, Dept Chem, I-20131 Milan, Italy
[2] Univ Pavia, Dept Pharmaceut Chem, I-27100 Pavia, Italy
来源：
ORGANIC LETTERS | 1999年 / 1卷 / 02期
关键词：
D O I：
10.1021/ol990594e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Nonactivated hydrocarbon sites of enantiopure compounds are oxyfunctionalized enantiospecifically by perfluoro-cis-2-n-butyl-3-n-propyloxaziridine under remarkably mild reaction conditions. The reaction occurs with retention of configuration at the oxidized stereogenic center, and the enantiospecificity is highly independent from both the carbon framework of the substrate and the presence of functional groups.
引用
收藏
页码：281 / 284
页数：4
相关论文
共 65 条
[1]   OXYGEN ATOM INSERTION INTO THE BENZYLIC CARBON HYDROGEN-BOND OF (R)-(-)-2-PHENYLBUTANE BY METHYL(TRIFLUOROMETHYL)DIOXIRANE - AN EFFICIENT AND MILD REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (S)-(-)-2-PHENYL-2-BUTANOL [J].
ADAM, W ;
ASENSIO, G ;
CURCI, R ;
GONZALEZNUNEZ, ME ;
MELLO, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :953-955
[2]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[3]   Epoxidation and oxygen insertion into alkane CH bonds by dioxirane do not involve detectable radical pathways [J].
Adam, W ;
Curci, R ;
D'Accolti, L ;
Dinoi, A ;
Fusco, C ;
Gasparrini, F ;
Kluge, R ;
Paredes, R ;
Schulz, M ;
Smerz, AK ;
Veloza, LA ;
Weinkotz, S ;
Winde, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (01) :105-109
[4]   Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2,3-dialkyloxaziridines. [J].
Arnone, A ;
Metrangolo, P ;
Novo, B ;
Resnati, G .
TETRAHEDRON, 1998, 54 (27) :7831-7842
[5]   Conversion of thio- and selenophosphoryl into phosphoryl group by perfluoro cis-2,3-dialkyloxaziridines [J].
Arnone, A ;
Novo, B ;
Pregnolato, M ;
Resnati, G ;
Terreni, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6401-6403
[6]   PERFLUORO-CIS-2,3-DIALKYLOXAZIRIDINES - EFFECTIVE REAGENTS FOR THE SELECTIVE OXIDATION OF ETHERS TO CARBONYL-COMPOUNDS [J].
ARNONE, A ;
BERNARDI, R ;
CAVICCHIOLI, M ;
RESNATI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2314-2315
[7]   Selective epoxidation of olefins by perfluoro-cis-2,3-dialkyloxaziridines [J].
Arnone, A ;
DesMarteau, DD ;
Novo, B ;
Petrov, VA ;
Pregnolato, M ;
Resnati, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8805-8810
[8]   DIRECT OXYFUNCTIONALIZATION AT UNACTIVATED SITES - SYNTHESIS OF 5-BETA-HYDROXYSTEROIDS BY PERFLUORODIALKYLOXAZIRIDINES [J].
ARNONE, A ;
CAVICCHIOLI, M ;
MONTANARI, V ;
RESNATI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5511-5513
[9]   The oxidation of alkanes with dimethyldioxirane; A new mechanistic insight [J].
Asensio, G ;
Mello, R ;
GonzalezNunez, ME ;
Boix, C ;
Royo, J .
TETRAHEDRON LETTERS, 1997, 38 (13) :2373-2376
[10]   Oxyfunctionalization of aliphatic esters by methyl(trifluoromethyl)dioxirane [J].
Asensio, G ;
Castellano, G ;
Mello, R ;
Nunez, MEG .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5564-5566
1234567