THE SYNTHESIS OF AZA[N]LADDERANES AND AZAHOMO[N]LADDERANES CONTAININGBETA-LACTAMS AT THE TERMINUS

Authors
WARRENER RN RUSSELL RA MARGETIC D
Citation
Rn. Warrener et al., THE SYNTHESIS OF AZA[N]LADDERANES AND AZAHOMO[N]LADDERANES CONTAININGBETA-LACTAMS AT THE TERMINUS, Synlett, (1), 1997, pp. 38
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
1
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):1<38:TSOAAA>2.0.ZU;2-1
Abstract
5-Azabicyclo[2.2.0]hex-2-en-6-one 1 undergoes [2 pi+2 pi] cycloadditio n with dimethyl acetylene dicarboxylate (Ru-catalysed) to yield aza[3] ladderane 2 which is transformed to aza[5]ladderanes 4 and 5 on treatm ent with cyclobutadiene and to azahomo[5]ladderanes 10 and 11 on react ion with cyclopentadiene. The specificities of these cycloaddition rea ctions are in agreement with predictions made using ab initio calculat ions. Chlorosulfonyl iso cyan ate addition is used to access azahomo[4 ]ladderane 14.