Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

1999 ◽  
Vol 40 (8) ◽  
pp. 1515-1518 ◽  
Author(s):  
Ilhyong Ryu ◽  
Shin-ichi Ogura ◽  
Satoshi Minakata ◽  
Mitsuo Komatsu
Keyword(s):  
Radical Cyclization ◽  
Imino Group ◽  
Vinyl Radical

ChemInform Abstract: Vinyl Radical Cyclization onto Imino Group. Selective 6-endo Cyclization onto Aldimines Leading to 3-Methylenepiperidines.

ChemInform ◽  
2010 ◽  
Vol 30 (20) ◽  
pp. no-no
Author(s):  
Ilhyong Ryu ◽  
Shin-ichi Ogura ◽  
Satoshi Minakata ◽  
Mitsuo Komatsu
Keyword(s):  
Radical Cyclization ◽  
Imino Group ◽  
Vinyl Radical

scholarly journals A Vinyl Radical Cyclization Route to Hydroxycyclohexene Fused Carbocycles

2016 ◽  
Vol 28 (1) ◽  
pp. 233-234 ◽  
Author(s):  
Shiladitya Chaudhuri ◽  
Susama Maity ◽  
Mahua Roy ◽  
Paramita Ray ◽  
Jayanta K. Ray
Keyword(s):  
Radical Cyclization ◽  
Vinyl Radical

scholarly journals Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

2013 ◽  
Vol 9 ◽  
pp. 1326-1332 ◽  
Author(s):  
Koichiro Miyazaki ◽  
Yu Yamane ◽  
Ryuichiro Yo ◽  
Hidemitsu Uno ◽  
Akio Kamimura
Keyword(s):  
Silicon Atom ◽  
Cascade Reaction ◽  
Radical Cyclization ◽  
Optically Active ◽  
Unsaturated Ester ◽  
Terminal Alkyne ◽  
Silyl Radical ◽  
Vinyl Radical ◽  
Radical Cascade ◽  
Carbonyl Radical

Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.

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