[Bis(2-pyridyldimethylsilyl)methyl]lithium. New reagent for the stereoselective synthesis of vinylsilanes

被引:42
作者
Itami, K [1 ]
Nokami, T [1 ]
Yoshida, J [1 ]
机构
[1] Kyoto Univ, Dept Synth Chem & Biol Chem, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol005735n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The generation of (2-PyMe2Si)(2)CHLi was easily accomplished by the deprotonation of (2-PyMe2Si)(2)CH2 using n-BuLi in Et2O. Thus generated (2-PyMe2Si)(2)CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities.
引用
收藏
页码:1299 / 1302
页数:4
相关论文
共 46 条
[1]  
ABELE BC, 1998, ORGANOSILICON CHEM, V3, P206
[2]  
Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01
[4]   PREPARATION OF ALPHA-SILYLCARBANIONS [J].
AGER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01) :168-170
[5]   A NEW ALKYLLITHIUM REAGENT FOR THE DIRECT CONVERSION OF ALDEHYDES AND KETONES TO VINYLSILANES [J].
BATES, TF ;
THOMAS, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1784-1785
[6]   STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].
BEAK, P ;
MEYERS, AI .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363
[7]   COUNTERION EFFECTS ON GEOMETRIC CONTROL IN THE PETERSON REACTION OF BISTRIMETHYLSILYL ESTERS - SYNTHETIC SCOPE AND MECHANISTIC IMPLICATIONS [J].
BOECKMAN, RK ;
CHINN, RL .
TETRAHEDRON LETTERS, 1985, 26 (41) :5005-5008
[8]  
Brook M. A, 2000, SILICON ORGANIC ORGA
[9]   Complex induced proximity effect enhancement in alpha-silyl carbanion generation. A general conversion of 2-silyl benzamides into 2-fluorosilylacetophenones [J].
Brough, PA ;
Fisher, S ;
Zhao, BP ;
Thomas, RC ;
Snieckus, V .
TETRAHEDRON LETTERS, 1996, 37 (17) :2915-2918
[10]   THE DIELS-ALDER ROUTE TO ALLYLSILANES FROM 1-TRIMETHYLSILYLBUTADIENES [J].
CARTER, MJ ;
FLEMING, I ;
PERCIVAL, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2415-2434