Azomethine ylides from tin-substituted cyclic carbinol amides: a new route to highly substituted pyrrolizidines.
[reaction: see text] Addition of organolithium and organomagnesium reagents to N-(tri-n-butylstannylmethyl)phthalimides yields N-(tri-n-butylstannylmethyl) cyclic carbinol amides, which form azomethine ylides upon treatment with HF.pyridine. This novel route to azomethine ylides allows rapid access to highly functionalized pyrrolizidines (1,2,3,9b-tetrahydropyrrolo[2,1-a]isoindol-5-ones).
Pearson
William H
WH
Department of Chemistry, University of Michigan, 930 North University Ave., Ann Arbor, Michigan 48109-1055, USA. wpearson@berryassoc.com
Dietz
Amber
A
Stoy
Patrick
P
D000577:Amides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008094:Lithium; D000432:Methanol / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D014001:Tin
D000577:Amides; D006571:Heterocyclic Compounds; D010797:Phthalimides; D011763:Pyrrolizidine Alkaloids; D014001:Tin; D008094:Lithium; D000432:Methanol