Rh(II)-catalyzed intramolecular N-H insertion of D-glucose-derived delta-amino alpha-diazo beta-ketoester: Synthesis of pyrrolidine iminosugars

TitleRh(II)-catalyzed intramolecular N-H insertion of D-glucose-derived delta-amino alpha-diazo beta-ketoester: Synthesis of pyrrolidine iminosugars
Publication TypeJournal Article
Year of Publication2007
AuthorsVyavahare, VP, Chattopadhyay, S, Puranik, VG, Dhavale, DD
JournalSynlett
Issue4
Pagination559-562
Date PublishedMAR
Type of ArticleArticle
ISSN0936-5214
Keywordsalkaloids, azasugars, carbohydrates, N-H insertion, Pyrrolidines, rhodium carbenoid
Abstract

The rhodium acetate catalyzed reaction of D-glucose-derived delta-amino alpha-diazo beta-ketoester allows a stereoselective beta-facial intramolecular N-H insertion reaction that leads to formation of the bicyclic pyrrolidinone ring skeleton in high yield. The sugar-substituted pyrrolidinone thus obtained was elaborated to allow the synthesis of promising glycosidase inhibitors, namely, 2,5-dideoxy2,5-imino-L-glycero-alpha-D-galactoheptitol and 2,5-dideoxy-2,5-imino-D-galactitol.

DOI10.1055/s-2007-970743
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.323

Divison category: 
Center for Material Characterization (CMC)
Physical and Materials Chemistry