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Neighboring group participation in the additions of iodonium and bromonium ions to N-alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n = 1,2).

Grant R GR Krow, Deepa D Gandla, Weiwei W Guo, Ryan A RA Centafont, Guoliang G Lin, Charles C DeBrosse, Philip E PE Sonnet, Charles W Ross CW Iii, Harri G HG Ramjit, Patrick J PJ Carroll, and Kevin C KC Cannon

J Org Chem 73(6):2114-21 (2008) PMID 18290656

Additions of iodonium-X reagents to N-alkoxycarbonyl-2-azabicyclo[2.2.1]hept-5-enes and the homologous 2-azabicyclo[2.2.2]oct-5-enes have been found to mirror the outcomes of additions of bromonium-X reagents. Only rearranged products were observed for reactions of either of these halonium ion reagents with the azabicylo[2.2.1]hept-5-enes. For the azabicyclo[2.2.2]oct-5-enes, nitrogen participation in addition of IOH or BrOH was dependent on the N-alkoxycarbonyl group. With larger N-Boc, N-Cbz, or N-Troc protecting groups, unrearranged 5-anti-hydroxy-6-syn-I(or Br)-2-azabicyclo[2.2.2]octanes were formed by nucleophilic attack at C(5) on syn-halonium ions. The structure of N-methyl-8-anti-bromo-4-anti-hydroxy-2-azabicyclo[3.2.1]octane has been reassigned by X-ray analysis.

DOI: 10.1021/jo702153q
Version: za2963e q8zac q8zbd q8zce q8zdb q8ze9 q8zf4 q8zg6

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