The Synthesis of Aza[n]ladderanes and Azahomo[n]ladderanes Containing β-Lactams at the Terminus

Ronald N. Warrener; Richard A. Russell; Davor Margetic

doi:10.1055/s-1997-697

Synlett 1997; 1997(1): 38-40
DOI: 10.1055/s-1997-697

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Synthesis of Aza[n]ladderanes and Azahomo[n]ladderanes Containing β-Lactams at the Terminus

Ronald N. Warrener^* , Richard A. Russell, Davor Margetic

^*Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia, Fax +61 79 30 9917; internet r.warrener@cqu.edu.au

Abstract

PDF Download All articles of this category

5-Azabicyclo[2.2.0]hex-2-en-6-one 1 undergoes [2π+2π] cycloaddition with dimethyl acetylene dicarboxylate (Ru-catalysed) to yield aza[3]ladderane 2 which is transformed to aza[5]ladderanes 4 and 5 on treatment with cyclobutadiene and to azahomo[5]ladderanes 10 and 11 on reaction with cyclopentadiene. The specifities of these cycloaddition reactions are in agreement with predictions made using ab initio calculations. Chlorosulfonylisocyanate addition is used to access azahomo[4]ladderane 14.

cycloaddition-specifities - polycyclobutanes - chlorosulfonyl isocyanate - ab initio calculations - 5-azabicyclo[2.2.0]hex-2-en-6-one

PDF (290 kb)