Show simple item record

dc.contributor.authorBroustal, Garance
dc.contributor.authorAriza, Xavier
dc.contributor.authorCampagne, Jean-Marc
dc.contributor.authorGarcia, Jordi
dc.contributor.authorGeorges, Yohan
dc.contributor.authorMarinetti, Angela
dc.contributor.authorRobiette, Raphaël
dc.date.accessioned2017-05-03T16:59:01Z
dc.date.available2017-05-03T16:59:01Z
dc.date.issued2007
dc.date.modified2009-12-07T03:37:44Z
dc.identifier.issn1434-193X
dc.identifier.doi10.1002/ejoc.200700503
dc.identifier.urihttp://hdl.handle.net/10072/27137
dc.description.abstractDirect enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition). The obtained -hydroxyesters were reduced to pent-2-ene-1,5-diols, which were converted into the corresponding dicarbamates with tosyl isocyanate. Stereoselective cyclization of these dicarbamates proceeded with 1,3-asymmetric induction under either thermodynamic or kinetic control to afford enantioselectively six-membered-ring cyclic carbamates. Calculations enabled us to rationalize the observed stereoselectivity.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley-VCH Verlag GmbH & Co.
dc.publisher.placeWeinheim
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom4293
dc.relation.ispartofpageto4297
dc.relation.ispartofissue26
dc.relation.ispartofjournalEuropean Journal of Organic Chemistry
dc.relation.ispartofvolume2007
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.titleA Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2007
gro.hasfulltextNo Full Text
gro.griffith.authorBroustal, Garance RJ.


Files in this item

FilesSizeFormatView

There are no files associated with this item.

This item appears in the following Collection(s)

  • Journal articles
    Contains articles published by Griffith authors in scholarly journals.

Show simple item record