a new method for the synthesis of Z-enediones via IBX-mediated oxidative rearrangement of 2-alkynyl alcohol systems

被引:41
作者
Crone, B [1 ]
Kirsch, SF [1 ]
机构
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
关键词
D O I
10.1039/b515838a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
o-Iodoxybenzoic acid (IBX) was found to mediate the conversion of alpha-alkynyl alcohols into Z-enediones under notably mild conditions via a novel rearrangement mechanism (33-65% yield, 13 examples).
引用
收藏
页码:764 / 766
页数:3
相关论文
共 33 条
[1]   OXIDATION OF FURANS WITH DIMETHYLDIOXIRANE [J].
ADGER, BM ;
BARRETT, C ;
BRENNAN, J ;
MCKERVEY, MA ;
MURRAY, RW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1553-1554
[2]  
Del Zotto A, 2000, EUR J ORG CHEM, V2000, P2795, DOI 10.1002/1099-0690(200008)2000:15<2795::AID-EJOC2795>3.0.CO
[3]  
2-8
[4]   Hypervalent iodine oxidants: Structure and kinetics of the reactive intermediates in the oxidation of alcohols and 1,2-diols by o-iodoxybenzoic acid (IBX) and Dess-Martin periodinane. A comparative H-1-NMR study [J].
DeMunari, S ;
Frigerio, M ;
Santagostino, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9272-9279
[6]   A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].
FRIGERIO, M ;
SANTAGOSTINO, M .
TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022
[7]   A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].
Frigerio, M ;
Santagostino, M ;
Sputore, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538
[8]  
Hartmann C., 1893, CHEM BER, V26, P1727
[9]  
Hirt UH, 2001, EUR J ORG CHEM, V2001, P1569
[10]   IBX-Mediated α-hydroxylation of α-alkynyl carbonyl systems.: A convenient method for the synthesis of tertiary alcohols [J].
Kirsch, SF .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10210-10212