Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles.
The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.
Anderson
Laura L
LL
Department of Chemistry, University of California, Irvine, California 92697, USA.
Woerpel
K A
KA
D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001888:Boric Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*
D000588:Amines; D000605:Amino Alcohols; D001372:Aza Compounds; D001888:Boric Acids; D003517:Cyclopentanes; D009570:Nitriles; D002244:Carbon; D003300:Copper; C032688:boric acid; D012825:Silicon