126908-53-0Relevant articles and documents
Asymmetric radical cyclizations: The synthesis of 6-alkyl pyrrolizidin-2-ones
Keusenkothen,Smith
, p. 2977 - 2992 (1992)
This work describes the use of ethyl (5S)-carboethoxy-2-pyrrolidinone (ethyl pyroglutamate) as a chiral starting material for use in radical cyclization reactions. Pyroglutamate is converted to a 5-iodomethyl-N-allylic-2-pyrrolidinone that undergoes radical cyclization under mild conditions. The products are 6-substituted pyrrolizidinone derivatives, produced with high diastereoselectivity.
AN IMPROVED REDUCTION OF THE ESTER MOIETY IN N-SUBSTITUTED PYROGLUTAMATES
Keusenkothen, Paul F.,Smith, Michael B.
, p. 2859 - 2868 (2007/10/02)
Lithium borohydride reduction of N-functionalized pyroglutamates failed to give the corresponding hydroxymethyl derivative.Reduction with lithium aluminium hydride bound to dry silica gel, however, gace excellent yields of chiral 5-hydroxymethyl-1-allyl-2
ASYMMETRIC SYNTHESIS OF PYRROLIZIDINONES BY RADICAL CYCLIZATION OF N-ALLYLIC PYROGLUTAMATES
Keusenkothen, Paul F.,Smith, Michael B.
, p. 3369 - 3372 (2007/10/02)
Ethyl S-pyroglutamate is converted to N-allylic-S C5-iodomethyl-2-pyrrolidinone.Facile radical cyclization on treatment with AIBN and tributyltin hydride in refluxing benzene gives good yields of the C6 substituted pyrrolizidin-2-one