INTRAMOLECULAR ANODIC OLEFIN COUPLING REACTIONS - THE USE OF ALLYLSILANES AND VINYLSILANES IN THE CONSTRUCTION OF QUATERNARY CARBONS

被引:17
作者
MOELLER, KD
HUDSON, CM
TINAOWOOLDRIDGE, LV
机构
关键词
D O I
10.1021/jo00065a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular anodic olefin coupling reactions involving the use of either an allylsilane as one of the olefin participants or a vinylsilane as part of a temporary silicon tether have been shown to be compatible with the formation of quaternary carbons.
引用
收藏
页码:3478 / 3479
页数:2
相关论文
共 24 条
[1]   ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - SELECTIVE AND VERSATILE TOTAL SYNTHESES OF THE ENANTIOMERS OF ALPHA-CUPARENONE AND BETA-CUPARENONE FROM A COMMON OPTICALLY-ACTIVE PRECURSOR [J].
CANET, JL ;
FADEL, A ;
SALAUN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3463-3473
[2]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - THE EFFECT ON STEREOSELECTIVITY OF ALLYLIC SUBSTITUTION [J].
CRAIG, D ;
READER, JC .
TETRAHEDRON LETTERS, 1992, 33 (28) :4073-4076
[3]   DIRECT ASYMMETRIC-SYNTHESIS OF QUATERNARY CARBON CENTERS VIA ADDITION ELIMINATION PROCESS - NITROOLEFINATION OF ALPHA-SUBSTITUTED DELTA-LACTONES [J].
FUJI, K ;
NODE, M ;
NAGASAWA, H ;
NANIWA, Y ;
TAGA, T ;
MACHIDA, K ;
SNATZKE, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :7921-7925
[4]   THE UNSYMMETRICAL SILAKETAL AS A NEUTRAL, REMOVABLE TETHER FOR EFFECTING INTRAMOLECULAR DIELS-ALDER REACTIONS [J].
GILLARD, JW ;
FORTIN, R ;
GRIMM, EL ;
MAILLARD, M ;
TJEPKEMA, M ;
BERNSTEIN, MA ;
GLASER, R .
TETRAHEDRON LETTERS, 1991, 32 (09) :1145-1148
[5]   INTRAMOLECULAR ANODIC OLEFIN COUPLING REACTIONS - A USEFUL METHOD FOR CARBON-CARBON BOND FORMATION [J].
HUDSON, CM ;
MARZABADI, MR ;
MOELLER, KD ;
NEW, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7372-7385
[6]   RADICAL CYCLIZATION OF (BROMOMETHYL)DIMETHYLSILYL PROPARGYL ETHERS - REGIOSELECTIVITY, CHEMOSELECTIVITY, AND STEREOSELECTIVITY [J].
JOURNET, M ;
MALACRIA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3085-3093
[7]   CHIRALITY TRANSMISSION INVOLVING A FREE-RADICAL-MEDIATED 6-EXO CYCLIZATION PROCESS - STEREOCONTROLLED SYNTHESIS OF BRANCHED-CHAIN 1,4-DIOLS [J].
KOREEDA, M ;
HAMANN, LG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8175-8177
[8]   OXIDATIVE ORGANIC ELECTROCHEMISTRY - A NOVEL INTRAMOLECULAR COUPLING OF ELECTRON-RICH OLEFINS [J].
MOELLER, KD ;
MARZABADI, MR ;
NEW, DG ;
CHIANG, MY ;
KEITH, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6123-6124
[9]   INTRAMOLECULAR ANODIC OLEFIN COUPLING REACTIONS - THE USE OF BIS ENOL ETHER SUBSTRATES [J].
MOELLER, KD ;
TINAO, LV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :1033-1041
[10]   INTRAMOLECULAR ANODIC OLEFIN COUPLING REACTIONS - THE USE OF ALLYSILANES [J].
MOELLER, KD ;
HUDSON, CM .
TETRAHEDRON LETTERS, 1991, 32 (21) :2307-2310