TiCl4 and LiClO4 promoted additions of O-silylketene acetals to chiral beta-formyl esters

被引:2
作者
Angert, H [1 ]
Czerwonka, R [1 ]
Reissig, HU [1 ]
机构
[1] TECH UNIV DRESDEN,INST ORGAN CHEM,D-01062 DRESDEN,GERMANY
来源
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1997年 / 339卷 / 05期
关键词
D O I
10.1002/prac.19973390179
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Lewis acid promoted additions of O-silylketene acetals 1a and 1b to beta-formyl ester 2 furnished gamma-lactones 3a and 3b. Employing TiCl4 as promotor chelate control leads to moderate or excellent trans selectivity, whereas LiClO4 as Lewis acid did not induce appreciable diastereoselectivity.
引用
收藏
页码:453 / 455
页数:3
相关论文
共 24 条
[1]   Chelate-controlled additions of titanium and lithium enolates to chiral beta-formyl esters - Diastereofacial and simple diastereoselectivity [J].
Angert, H ;
Schumacher, R ;
Reissig, HU .
CHEMISCHE BERICHTE, 1996, 129 (02) :227-232
[2]  
Angert H, 1996, LIEBIGS ANN, P259
[3]  
ANGERT H, 1992, TETRAHEDRON, V48, P5681
[4]  
ANGERT H, 1995, THESIS TU DRESDEN
[5]   [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS AT AMBIENT-TEMPERATURE IN 3.0M LITHIUM PERCHLORATE-DIETHYL ETHER [J].
GRIECO, PA ;
CLARK, JD ;
JAGOE, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5488-5489
[6]   DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED [J].
GRIECO, PA ;
NUNES, JJ ;
GAUL, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4595-4596
[7]   LITHIUM PERCHLORATE CATALYZED CONJUGATE ADDITION OF O-SILYLATED KETENE ACETALS TO HINDERED ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS AT ATMOSPHERIC-PRESSURE [J].
GRIECO, PA ;
COOKE, RJ ;
HENRY, KJ ;
VANDERROEST, JM .
TETRAHEDRON LETTERS, 1991, 32 (36) :4665-4668
[8]   CHELATION CONTROLLED ADDITION OF ALLYLSTANNANES TO ALDEHYDES IN LITHIUM PERCHLORATE-DIETHYL ETHER [J].
HENRY, KJ ;
GRIECO, PA ;
JAGOE, CT .
TETRAHEDRON LETTERS, 1992, 33 (14) :1817-1820
[9]   ALKYLATION OF QUINONES BY O-SILYLATED KETENE ACETALS IN LICLO4-ETHER AS REACTION MEDIUM [J].
IPAKTSCHI, J ;
HEYDARI, A .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (06) :1513-1515
[10]   LICLO4-CATALYZED NUCLEOPHILIC-ADDITION TO ALPHA-CHIRAL ALDEHYDES, ALDIMINES, AND OXIRANES [J].
IPAKTSCHI, J ;
HEYDARI, A .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1905-1912