Fragmentation of peroxyhemiacetals. Stereoselective synthesis of 1,2-dioxolanes

被引:11
作者
Hernandez, R
Velazquez, SM
Suarez, E
Prange, T
机构
[1] CSIC,INST PROD NAT & AGROBIOL,LA LAGUNA 38206,TENERIFE,SPAIN
[2] UNIV PARIS 11,LURE,F-91405 ORSAY,FRANCE
关键词
D O I
10.1016/0040-4039(96)01360-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient approach to the synthesis of 1,2-dioxolanes by beta-fragmentation of alkoxy radicals from readily available peroxyhemiacetals, under mild conditions, is described. The radical reaction proceeds in a diastereoselective manner providing a sale 1,2-dioxolane. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6409 / 6412
页数:4
相关论文
共 49 条
[1]   BICYCLIC ENDOPEROXIDES AND SYNTHETIC APPLICATIONS [J].
BALCI, M .
CHEMICAL REVIEWS, 1981, 81 (01) :91-108
[2]   REVERSIBLE COUPLING OF A SUBSTITUTED ALLYLIC RADICAL WITH MOLECULAR-OXYGEN IN A TOCO REACTION OF 5-METHYLHEPTA-1,3,6-TRIENE [J].
BARKER, PJ ;
BECKWITH, ALJ ;
FUNG, Y .
TETRAHEDRON LETTERS, 1983, 24 (01) :97-100
[3]   STEREOCHEMICAL CONTROL IN CYCLIZATION TO BICYCLIC DIOXOLANES [J].
BEGLEY, MJ ;
FLETCHER, RJ ;
MURPHY, JA ;
SHERBURN, MS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (23) :1723-1725
[4]   OXYMETALATION .24. PREPARATION OF CYCLIC PEROXIDES BY CYCLOPEROXYMERCURIATION OF UNSATURATED HYDROPEROXIDES [J].
BLOODWORTH, AJ ;
CURTIS, RJ ;
SPENCER, MD ;
TALLANT, NA .
TETRAHEDRON, 1993, 49 (13) :2729-2750
[5]   A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group [J].
Bloodworth, AJ ;
Bothwell, BD ;
Collins, AN ;
Maidwell, NL .
TETRAHEDRON LETTERS, 1996, 37 (11) :1885-1888
[6]   Tandem carbon-radical peroxidation-addition to carbonyl groups reaction. A new synthesis of steroidal beta-peroxy lactones [J].
Boto, A ;
Hernandez, R ;
Suarez, E ;
Betancor, C ;
Rodriguez, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8209-8217
[7]   A NEW SEQUENTIAL ALKOXY RADICAL FRAGMENTATION OF DELTA-HYDROXYKETONES [J].
BOTO, A ;
HERNANDEZ, R ;
SUAREZ, E .
TETRAHEDRON LETTERS, 1994, 35 (16) :2597-2600
[8]   CONCISE SYNTHESIS OF YINGZHAOSU-C AND EPI-YINGZHAOSU-C BY PEROXYL RADICAL CYCLIZATION - ASSIGNMENT OF RELATIVE CONFIGURATION [J].
BOUKOUVALAS, J ;
POULIOT, R ;
FRECHETTE, Y .
TETRAHEDRON LETTERS, 1995, 36 (24) :4167-4170
[9]   PREPARATION, PROPERTIES, AND REACTIONS OF CARBONYL OXIDES [J].
BUNNELLE, WH .
CHEMICAL REVIEWS, 1991, 91 (03) :335-362
[10]   PHOTOSENSITIZED OXIDATION OF MODEL UNSATURATED LIPID SYSTEMS - (4Z,7Z)-UNDECA-4,7-DIENE AND (4Z)-UNDEC-4-EN-7-YNE [J].
CARLESS, HAJ ;
BATTEN, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (09) :1999-2007