Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations

2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible usin...

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Published inChemical science (Cambridge) Vol. 6; no. 6; pp. 3550 - 3555
Main Authors Burns, Alan R., Madec, Amaël G. E., Low, Darryl W., Roy, Iain D., Lam, Hon Wai
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 01.06.2015
Subjects
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Chemistry
Methodology
Olefins
Synthesis
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ISSN2041-6520
2041-6539
DOI10.1039/C5SC00753D

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Summary:2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible using this methodology.
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These authors contributed equally.
ISSN:2041-6520
2041-6539
DOI:10.1039/C5SC00753D