Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes

被引：18
作者：
Chan, WK
Wong, MK
Che, CM
机构：
[1] Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Dept Chem, Open Lab Chem Biol, Hong Kong, Hong Kong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 11期
关键词：
D O I：
10.1021/jo047733c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals.
引用
收藏
页码：4226 / 4232
页数：7
相关论文
共 69 条
[11]   Total synthesis and antitubulin activity of C10 analogues of cryptophycin-24 [J].
Buck, SB ;
Huff, JK ;
Himes, RH ;
Georg, GI .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (03) :696-702
[12]   Highly diastereoselective epoxidation of allyl-substituted cycloalkenes catalyzed by metalloporphyrins [J].
Chan, WK ;
Liu, P ;
Yu, WY ;
Wong, MK ;
Che, CM .
ORGANIC LETTERS, 2004, 6 (10) :1597-1599
[13]   Mechanistic insight into the inactivation of carboxypeptidase A by α-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid, a novel type of irreversible inhibitor for carboxypeptidase A with no stereospecificity [J].
Chung, SJ ;
Chung, S ;
Lee, HS ;
Kim, EJ ;
Oh, KS ;
Choi, HS ;
Kim, KS ;
Kin, YJ ;
Hahn, JH ;
Kim, DH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6462-6471
[14]   REGIOSELECTIVE AND ENANTIOSELECTIVE EPOXIDATION CATALYZED BY METALLOPORPHYRINS [J].
COLLMAN, JP ;
ZHANG, XM ;
LEE, VJ ;
UFFELMAN, ES ;
BRAUMAN, JI .
SCIENCE, 1993, 261 (5127) :1404-1411
[15]   EPOXIDATION OF OLEFINS BY CYTOCHROME-P-450 MODEL COMPOUNDS - KINETICS AND STEREOCHEMISTRY OF OXYGEN ATOM TRANSFER AND ORIGIN OF SHAPE SELECTIVITY [J].
COLLMAN, JP ;
BRAUMAN, JI ;
MEUNIER, B ;
HAYASHI, T ;
KODADEK, T ;
RAYBUCK, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2000-2005
[16]   SHAPE-SELECTIVE OLEFIN EPOXIDATION CATALYZED BY MANGANESE PICNIC BASKET PORPHYRINS [J].
COLLMAN, JP ;
ZHANG, XM ;
HEMBRE, RT ;
BRAUMAN, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5356-5357
[17]   Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].
Danishefsky, SJ ;
Bilodeau, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419
[18]   METALLOPORPHYRIN-CATALYSED EPOXIDATION OF TERMINAL ALIPHATIC OLEFINS WITH HYPOCHLORITE SALTS OR POTASSIUM HYDROGEN PERSULFATE [J].
DEPOORTER, B ;
MEUNIER, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (11) :1735-1740
[19]   Polyhaloporphyrins: Unusual ligands for metals and metal-catalyzed oxidations [J].
Dolphin, D ;
Traylor, TG ;
Xie, LY .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (06) :251-259
[20]   Deprotection and direct oxidative deprotection of trimethylsilyl ethers to their corresponding alcohols and carbonyl compounds with tris[trinitratocerium(IV)] paraperiodate, [(NO3)(3)Ce](3).H2IO6, in an aprotic solvent [J].
Firouzabadi, H ;
Shiriny, F .
SYNTHETIC COMMUNICATIONS, 1996, 26 (03) :423-432
1234567