Stereoselective synthesis of 2,6-cis- and 2,6-trans-piperidines through organocatalytic aza-Michael reactions: a facile synthesis of (+)-myrtine and (-)-epimyrtine.
Both 2,6-cis- and 2,6-trans-piperidines were prepared from common substrates through organocatalytic aza-Michael reactions promoted by the gem-disubstituent effect in conjunction with dithiane coupling reactions. The organocatalytic aza-Michael reaction enabled a facile synthesis of (+)-myrtine and (-)-epimyrtine from a common substrate.
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Yongcheng
Y
Ying
Hyoungsu
H
Kim
Jiyong
J
Hong
D002384:Catalysis; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D010880:Piperidines; D011799:Quinazolines; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C482086:epimyrtine; C519820:myrtine