Facial selectivity of the sharpless bromine catalyzed aziridination

A bromine catalyzed aziridination reaction has been applied to 7,7-dibromo-3-norcarene, which resulted in a highly stereoselective route to cis-4,4-dibromo-8-(toluene-4-sulfonyl)-8-aza-tricyclo[5.1.0.0]octane in a 46% yield. In order to confirm the stereochemstry of the aziridination reaction trans-...

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Bibliographic Details
Published inHeterocycles Vol. 62; pp. 635 - 642
Main Authors Schmitt, AC, Smith, CM, Voight, EA, O'Doherty, GA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
bromonium ion
OLEFINS
beta-hydroxy azide
tosylaziridine
sharpless bromine-catalyzed arizidination
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Summary:A bromine catalyzed aziridination reaction has been applied to 7,7-dibromo-3-norcarene, which resulted in a highly stereoselective route to cis-4,4-dibromo-8-(toluene-4-sulfonyl)-8-aza-tricyclo[5.1.0.0]octane in a 46% yield. In order to confirm the stereochemstry of the aziridination reaction trans-4,4-ibromo-8-(toluene-4-sulfonyl)-8-aza-tricyclo [5.1.0.0]octane and its diastereoisomer cis-4,4-dibromo-8-(toluene-4-sulfonyl)-8-aza-tricyclo [5.1.0.0]octane were prepared in a stereoselective manner from the corresponding cis- and trans-7,7-dibromo-3-norcarene epoxides (61 and 9.2% yields, respectively). These three routes offer stereochemical proof for the stereo specificity of the bromine-catalyzed aziridination of hindered alkenes.
ISSN:0385-5414
1881-0942
DOI:10.3987/com-03-s(p)57