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Synlett 1998; 1998(6): 588-589
DOI: 10.1055/s-1998-3134
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A 1,3-Dipolar Cycloaddition Route to 7-Azanorbornanes: Application to the Synthesis of syn-Facial N-Bridged Polynorbornanes

Douglas N. Butler* , John R. Malpass, Davor Margetic, Richard A. Russell, Guangxing Sun, Ronald N. Warrener
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia
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Publication History

Publication Date:
31 December 2000 (online)

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Aziridinocyclobutenes react with electron-deficient or ring-strained alkenes to produce 7-azanorbornenes in a novel 1,3-dipolar cycloaddition reaction suitable for block assembly protocols. Benzo-7-azanorbornadiene and 7-heterobridged analogues react stereoselectively to produce compounds with syn-facial orientation of their bridges.

1,3-dipolar cycloaddition - stereospecific - invertomers - 7-azanorbornenes - aziridines