THE CONVERSION OF ALPHA-HYDROXY ESTERS TO BETA-HYDROXY ESTERS BY A DEOXYGENATION CONDENSATION REACTION PROMOTED BY SAMARIUM DIIODIDE

被引:21
作者
ENHOLM, EJ
JIANG, SJ
机构
[1] Department of Chemistry, University of Florida, Gainesville
基金
美国国家科学基金会;
关键词
SAMARIUM DIIODIDE; DEOXYGENATION; KETYL; BETA-ALKOXY ESTER;
D O I
10.1016/S0040-4039(00)74119-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild reaction sequence begins by transforming an alpha-hydroxy ester to an alpha-benzoate ester. Next, the alpha-benzoate ester is both reductively deoxygenated with samarium diiodide and subsequently condensed with a ketone present in the reaction mixture to afford a beta-hydroxy ester with two new alkyl appendages.
引用
收藏
页码:313 / 316
页数:4
相关论文
共 33 条
[21]   LANTHANIDES IN ORGANIC-SYNTHESIS .2. REDUCTION OF ALPHA-HETEROSUBSTITUTED KETONES [J].
MOLANDER, GA ;
HAHN, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1135-1138
[22]   LANTHANIDES IN ORGANIC-SYNTHESIS .3. A GENERAL PROCEDURE FOR 5-MEMBERED AND 6-MEMBERED RING ANNULATION [J].
MOLANDER, GA ;
ETTER, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1778-1786
[23]   INTRAMOLECULAR REDUCTIVE COUPLING REACTIONS PROMOTED BY SAMARIUM DIIODIDE [J].
MOLANDER, GA ;
KENNY, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8236-8246
[24]   REDUCTION OF VINYLOXIRANES WITH SAMARIUM DIIODIDE - AN EFFICIENT ROUTE TO FUNCTIONALIZED CHIRAL, NONRACEMIC (E)-ALLYLIC ALCOHOLS [J].
MOLANDER, GA ;
LABELLE, BE ;
HAHN, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5259-5264
[25]   LANTHANIDES IN ORGANIC-SYNTHESIS .8. 1,3-ASYMMETRIC INDUCTION IN INTRAMOLECULAR REFORMATSKY-TYPE REACTIONS PROMOTED BY SAMARIUM DIIODIDE [J].
MOLANDER, GA ;
ETTER, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6556-6558
[26]  
MOLANDER GA, 1989, CHEM METAL CARBON BO, V5, P319
[27]   LANTHANIDES IN ORGANIC-SYNTHESIS .20. A SHORT STEP SYNTHESIS OF FERRULACTONE-I [J].
MORIYA, T ;
HANDA, Y ;
INANAGA, J ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1988, 29 (52) :6947-6948
[28]   LANTHANIDES IN ORGANIC-SYNTHESIS [J].
NATALE, NR .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (06) :387-424
[29]  
OTSUBO K, 1987, TETRAHEDRON LETT, P4437
[30]  
PRATT DV, 1987, TETRAHEDRON LETT, P3065