Synthesis of heterocycles. Construction of the 1-azabicyclo[2.2.1]heptyl system by sequential ring-closure of acyclic β-ammonio substituted radicals

Treatment of an irradiated solution of 1-methyl-1-(2-propynyl)-1-bis(2-phenylselenylethyl)ammonium iodide in tert-amyl alcohol with tributyltin hydride is found to be an effective procedure for the synthesis of 1,4-dimethyl-1-azoniabicyclo-[2.2.1]heptane iodide. Attachment of a trimethylsilyl or phe...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 32; pp. 5805 - 5808
Main Authors Della, Ernest W, Knill, Andrew M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.08.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Treatment of an irradiated solution of 1-methyl-1-(2-propynyl)-1-bis(2-phenylselenylethyl)ammonium iodide in tert-amyl alcohol with tributyltin hydride is found to be an effective procedure for the synthesis of 1,4-dimethyl-1-azoniabicyclo-[2.2.1]heptane iodide. Attachment of a trimethylsilyl or phenyl substituent to the terminal carbon of the triple bond in the alkynyl salt leads to bridgehead-substituted bicyclic heterocyclic salts. Reduction of the quaternary ammonium selenides depicted with Bu 3SnH gives excellent yields of the heterocyclic salts.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01231-2