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 in | Chemical science (Cambridge) Vol. 6; no. 6; pp. 3550 - 3555 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
01.06.2015
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| Subjects | |
| Online Access | Get full text |
| ISSN | 2041-6520 2041-6539 |
| DOI | 10.1039/C5SC00753D |
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| Abstract | 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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| AbstractList | 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. 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. 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. |
| Author | Lam, Hon Wai Roy, Iain D. Burns, Alan R. Madec, Amaël G. E. Low, Darryl W. |
| AuthorAffiliation | b School of Chemistry , University of Nottingham , University Park , Nottingham , NG7 2RD , UK . Email: hon.lam@nottingham.ac.uk a EaStCHEM , School of Chemistry , University of Edinburgh , Joseph Black Building, The King's Buildings, David Brewster Road , Edinburgh , EH9 3FJ , UK |
| AuthorAffiliation_xml | – name: b School of Chemistry , University of Nottingham , University Park , Nottingham , NG7 2RD , UK . Email: hon.lam@nottingham.ac.uk – name: a EaStCHEM , School of Chemistry , University of Edinburgh , Joseph Black Building, The King's Buildings, David Brewster Road , Edinburgh , EH9 3FJ , UK |
| Author_xml | – sequence: 1 givenname: Alan R. surname: Burns fullname: Burns, Alan R. organization: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, David Brewster Road, Edinburgh, EH9 3FJ, UK., School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK – sequence: 2 givenname: Amaël G. E. surname: Madec fullname: Madec, Amaël G. E. organization: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK – sequence: 3 givenname: Darryl W. surname: Low fullname: Low, Darryl W. organization: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, David Brewster Road, Edinburgh, EH9 3FJ, UK – sequence: 4 givenname: Iain D. surname: Roy fullname: Roy, Iain D. organization: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, David Brewster Road, Edinburgh, EH9 3FJ, UK – sequence: 5 givenname: Hon Wai surname: Lam fullname: Lam, Hon Wai organization: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, David Brewster Road, Edinburgh, EH9 3FJ, UK., School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29511516$$D View this record in MEDLINE/PubMed |
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| Title | Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations |
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