CHELATION CONTROLLED ADDITION OF ALLYLSTANNANES TO ALDEHYDES IN LITHIUM PERCHLORATE-DIETHYL ETHER

被引:63
作者
HENRY, KJ [1 ]
GRIECO, PA [1 ]
JAGOE, CT [1 ]
机构
[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
关键词
D O I
10.1016/S0040-4039(00)74150-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alpha-Alkoxy aldehydes undergo chelation controlled addition of allylstannanes with high diastereoselectivity in the presence of 5.0 M lithium perchlorate in diethyl ether at ambient temperature and pressure.
引用
收藏
页码:1817 / 1820
页数:4
相关论文
共 11 条
[1]   ON THE COMMUNICATION OF CHIRALITY FROM FURANOSE AND PYRANOSE RINGS TO MONOSACCHARIDE SIDE-CHAINS - ANOMALOUS RESULTS IN THE GLUCOSE SERIES [J].
DANISHEFSKY, SJ ;
DENINNO, MP ;
PHILLIPS, GB ;
ZELLE, RE ;
LARTEY, PA .
TETRAHEDRON, 1986, 42 (11) :2809-2819
[2]   [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
[3]   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
[4]   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
[5]  
HENRY KJ, UNPUB
[6]   THE EFFECT OF PROTECTING GROUPS ON CHELATION CONTROL [J].
KAHN, SD ;
KECK, GE ;
HEHRE, WJ .
TETRAHEDRON LETTERS, 1987, 28 (03) :279-280
[7]   DIRECT EVIDENCE FOR THE ABSENCE OF CHELATION WITH BETA-SILYLOXY ALDEHYDES AND LEWIS-ACIDS [J].
KECK, GE ;
CASTELLINO, S .
TETRAHEDRON LETTERS, 1987, 28 (03) :281-284
[8]  
KECK GE, 1984, TETRAHEDRON LETT, V25, P265, DOI 10.1016/S0040-4039(00)99857-5
[9]  
Pereyre M., 1987, TIN ORGANIC SYNTHESI
[10]   ORGANOMETALLIC HIGH-PRESSURE REACTIONS - ALLYLATION OF ALDEHYDES WITH ALLYLIC STANNANES UNDER MILD CONDITIONS [J].
YAMAMOTO, Y ;
MARUYAMA, K ;
MATSUMOTO, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (09) :489-490