Optically active alpha-spirocyclopropyllactones and 3-aminopyrrolidones via stereoselective diazoalkane cycloaddition at alpha-alkylidenelactones

Authors
Otto, A Ziemer, B Liebscher, J
Citation
A. Otto et al., Optically active alpha-spirocyclopropyllactones and 3-aminopyrrolidones via stereoselective diazoalkane cycloaddition at alpha-alkylidenelactones, SYNTHESIS-S, (6), 1999, pp. 965-972
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
6
Year of publication
1999
Pages
965 - 972
Database
ISI
SICI code
0039-7881(199906):6<965:OAAA3V>2.0.ZU;2-4
Abstract
1,3-Dipolar cycloaddition of diazoalkanes 2 to optically active alpha-alkyl idenelactones 1 gives high yields of pyrazolines 3 and 4 in a stereoselecti ve manner. These pyrazolines can further be transformed into alpha-spirocyc lopropyllactones 5 and 6 by irradiation and into alpha-amino-alpha-(omega-h ydroxyalkyl)-gamma-butyrolactams 7 and 8 by reductive N-N bond cleavage.