Exploring the unique reactivities of heterobicyclic tetrazoles—access to functionally diverse and versatile heterocyclic scaffolds

The benzylic hydrogen atom in oxabicyclic tetrazoles such as (6 R,8 R)-(8-phenyl-5,6-dihydro-8 H-tetrazolo[5,1- c][1,4]oxazin-6-yl)-alkanols ( A, X=CH 2OH) is highly acidic, being alkylated in preference to a hydroxymethyl group with NaH and active alkyl halides. The enantioenriched products B now c...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 33; pp. 6656 - 6669
Main Authors Hanessian, Stephen, Deschênes-Simard, Benoît, Simard, Daniel
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.08.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONFORMATIONAL MIMICRY
RHAMNO-FURANOSES
CYCLOADDITION
AZIDES
MECHANISM
SYNTHETIC APPLICATIONS
CHEMISTRY
ACETALS
DERIVATIVES
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Summary:The benzylic hydrogen atom in oxabicyclic tetrazoles such as (6 R,8 R)-(8-phenyl-5,6-dihydro-8 H-tetrazolo[5,1- c][1,4]oxazin-6-yl)-alkanols ( A, X=CH 2OH) is highly acidic, being alkylated in preference to a hydroxymethyl group with NaH and active alkyl halides. The enantioenriched products B now contain a phenyl and alkyl group on a stereogenic benzylic carbon atom. The products are subject to β-elimination to give 1-{1-[3-propenyl]-1 H-tetrazol-5-yl}-1-phenyl-alkanols. Cleavage of the propenyl chain leads to chiral non-racemic 1-phenyl-1-(1 H-tetrazol-5-yl)-alkanols C. Free-radical ‘anomeric’ azidation of the oxabicyclic tetrazoles followed by reduction and ring closure with inversion of configuration produces azabicyclic tetrazoles D as constrained functionalized piperazines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.06.033