A DIRECT PREPARATION OF 1,2-DIACETATES FROM ALDEHYDES AND KETONES PROMOTED BY SAMARIUM DIIODIDE

被引:8
作者
ENHOLM, EJ
SATICI, H
机构
[1] Department of Chemistry, University of Florida, Gainesville
关键词
D O I
10.1016/S0040-4039(00)74346-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In a mild reaction mediated by samarium diiodide, ketones and aldehydes have been converted into 1,2-diacetates from commercially available bromomethyl acetate in a single synthetic transformation.
引用
收藏
页码:2433 / 2436
页数:4
相关论文
共 26 条
[1]   DIPOLE-STABILIZED CARBANIONS - DIRECT LITHIATION OF METHYL-GROUP OF A METHYL-ESTER [J].
BEAK, P ;
MCKINNIE, BG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :5213-5213
[2]  
COREY EJ, 1983, TETRAHEDRON LETT, P3163
[3]  
COREY EJ, 1983, TETRAHEDRON LETT, P3165
[4]   A ROUTE TO VICINAL DIAMINES FROM THE SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ALDIMINES [J].
ENHOLM, EJ ;
FORBES, DC ;
HOLUB, DP .
SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :981-987
[5]   LANTHANIDE INDUCED INTRAMOLECULAR COUPLING OF ALDEHYDES AND KETONES WITH ELECTRON-DEFICIENT OLEFINS [J].
ENHOLM, EJ ;
TRIVELLAS, A .
TETRAHEDRON LETTERS, 1989, 30 (09) :1063-1066
[6]   SAMARIUM(II) IODIDE MEDIATED CARBOCYCLES FROM CARBOHYDRATES - APPLICATION TO THE SYNTHESIS OF THE C-RING OF ANGUIDINE [J].
ENHOLM, EJ ;
SATICI, H ;
TRIVELLAS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5841-5843
[7]   SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES [J].
ENHOLM, EJ ;
TRIVELLAS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6463-6465
[8]   A SAMARIUM(II) IODIDE PROMOTED TANDEM RADICAL CYCLIZATION - THE TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND THE FORMAL SYNTHESIS OF (+/-)-CORIOLIN [J].
FEVIG, TL ;
ELLIOTT, RL ;
CURRAN, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5064-5067
[9]   SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE [J].
FUKUZAWA, S ;
NAKANISHI, A ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1669-1675
[10]   A NOVEL LANTHANIDE-INDUCED REARRANGEMENT [J].
HOLTON, RA ;
WILLIAMS, AD .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25) :5981-5983