0000000000406776
AUTHOR
Sandrine Deloisy
ChemInform Abstract: Stereoselective Synthesis of 2-Substituted Pyrrolidines.
Using O -pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, ( S ) or ( R ) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo -trig-cyclization of these N -glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.
ChemInform Abstract: A Novel Synthesis of Chain-Extended Amino Sugar Derivatives Through Aza-Cope Rearrangement of N-Galactosyl-N-homoallylamines.
Abstract Chain-extended amino sugars are synthesized via stereocontrolled Lewis acid-catalyzed aza-Cope rearrangement of N-glycosyl homoallylamines in high yield and stereoselectivity.
Stereoselective Synthesis of 2-Substituted Pyrrolidines
Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.
A novel synthesis of chain-extended amino sugar derivatives through aza-Cope rearrangement of N-galactosyl-N-homoallylamines
Abstract Chain-extended amino sugars are synthesized via stereocontrolled Lewis acid-catalyzed aza-Cope rearrangement of N-glycosyl homoallylamines in high yield and stereoselectivity.