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Synlett 2001; 2001(2): 0202-0205
DOI: 10.1055/s-2001-10789
DOI: 10.1055/s-2001-10789
letter
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Neighbouring Group Participation in N-Methoxymethyl 7-Azanorbornanes 1: The Synthesis of N,N′-Methano-bridged Diazasesquinorbornanes, N3-[3]Polynorbornanes and CN3-[4]Polynorbornanes
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2001 (online)
A new tandem route to N,N′-methano-bridged diazasesquinorbornanes is reported in which 7-azabenzonorbornadienes are reacted with ester-activated N-(methoxymethyl)aziridinocyclobutanes to form adducts which immediately undergo N,N′-methanobridge formation by nucleophilic attack of the nitrogen lone pair of one N-bridge onto the methoxymethyl group attached to the adjacent N-bridge. Alternative routes to N,N′-methano-bridged structures of this type are discussed.
neighbouring-group - cycloadditions - bicyclic compounds - stereoselectivity