Catalytic epoxide oxidation:: a novel access to flavouring and odorant α-diketones

被引:8
作者
Antoniotti, S
Alezra, N
Fernandez, X
Duñach, E
机构
[1] Univ Nice, Chim Bioorgan Lab, UMR 6001, CNRS,Fac Sci, F-06108 Nice 2, France
[2] Univ Nice, Lab Aromes Synth & Interact, Fac Sci, F-06108 Nice 2, France
关键词
alpha-diketone; flavouring compounds; epoxide; oxidation; 2,3-pentanedione;
D O I
10.1002/ffj.1371
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The catalytic oxidation of epoxides to alpha-diketones provides a novel access to a variety of flavouring compounds and odorants. This alternative synthetic strategy involves an oxidation reaction catalysed by commercially available reagents and affords four cyclic and acyclic alpha-diketones presenting interesting organoleptic properties. The availability of epoxides, easily obtained by olefin epoxidation, and the possibility of obtaining alpha-diketones with a variety of structures gives a high potential to this method. Copyright (C) 2004 John Wiley Sons, Ltd.
引用
收藏
页码:373 / 381
页数:9
相关论文
共 33 条
[1]   NEW METHOD OF PYRAZINE SYNTHESIS FOR FLAVOR USE [J].
AKIYAMA, T ;
ENOMOTO, Y ;
SHIBAMOTO, T .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1978, 26 (05) :1176-1179
[2]   Novel and catalytic oxidation of internal epoxides to α-diketones [J].
Antoniotti, S ;
Duñach, E .
CHEMICAL COMMUNICATIONS, 2001, (24) :2566-2567
[3]   (ACYLOXY)CARBENES FROM THERMOLYSIS OF OXADIAZOLINES IN SOLUTION - 1-ACETOXYETHYLIDENE AND 1-ACETOXYPROPYLIDENE [J].
BEKHAZI, M ;
WARKENTIN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4870-4873
[4]  
BELITZ HD, 1999, FOOD CHEM, P332
[5]  
BLOMMAERT K L J, 1976, Journal of South African Botany, V42, P121
[6]  
DHARMARATNE HRW, 1982, INDIAN J CHEM B, V21, P39
[7]   COMPOSITION OF BUCHU LEAF OIL [J].
FLUCK, AA ;
MITCHELL, W ;
PERRY, HM .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1961, 12 (04) :290-&
[8]  
Fraternale D., 1998, Journal of Essential Oil Research, V10, P568
[9]  
FURNISS BS, 1908, VOGELS TXB PRACTICAL, P412
[10]   ARYNIC CONDENSATION OF KETONE ENOLATES .17. NEW GENERAL ACCESS TO BENZOCYCLOBUTENE DERIVATIVES [J].
GREGOIRE, B ;
CARRE, MC ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1419-1427