Diastereoselective synthesis of a highly functionalized angularly substituted cis-perhydroisoquinoline-3,6-dione via organoiron.
Nitrile addition to cyclohexadienyium-Fe(CO)(3) perchlorate salt provides an efficient entry into the angularly substituted cis-fused perhydroisoquinoline ring system. The key steps in the assembly of the angularly substituted cis-octahydroisoquinoline ring are the transformation of the nitrile to an N-(benzylmethylencie)amino group and a diastereoselective intramolecular Michael reaction to form the bicyclic ring.
Han
Jeng-Liang
JL
Department of Chemistry, National Sun Yat Sen University, Kaohsiung, Taiwan 804.
Liu
Meng-Chi
MC
Ong
Chi Wi
CW
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D058085:Iron Compounds / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D058085:Iron Compounds; D007546:Isoquinolines; D009570:Nitriles; C549123:cis-perhydroisoquinoline-3,6-dione