A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres.
Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.
Koutsaplis
Magdaline
M
School of Chemistry, Monash University, Clayton, Melbourne, Vic 3800, Australia.
Andrews
Philip C
PC
Bull
Steven D
SD
Duggan
Peter J
PJ
Fraser
Benjamin H
BH
Jensen
Paul
P
D000499:Allylamine / Q000031:analogs & derivatives* / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry*; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C525830:(S)-N-(alpha-methylbenzyl)allylamine; D001372:Aza Compounds; D001593:Benzyl Compounds; D002934:Cinnamates; D003510:Cyclohexanes; C525829:tert-butyl cinnamate; D000499:Allylamine