A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.
A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (±)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.
Jiang
Tao
T
Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.
Livinghouse
Tom
T
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D005030:Ethylenes; D011763:Pyrrolizidine Alkaloids; C545571:xenovenine; C036216:ethylene; D012538:Scandium
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