Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/51348

TitleEnantioselective diels-alder cycloadditions in the synthesis of two enantiomeric sets of chiral polyhydroxylated pipecolic acid derivatives
Author(s)Duarte, Vera C. M.
Alves, Maria José Chão
Fortes, A. Gil
Keywordsenantioselectivity
Diels-Alder reaction
amino acids
asymmetric synthesis
azasugars
Issue date1-Jul-2014
PublisherGeorg Thieme Verlag
JournalSynlett
Abstract(s)(2E)-Penta-2,4-dien-1-ol was combined with electrophilic tert-butyl 2H-azirine-3-carboxylate by using a Lewis acid-catalyzed self-assembled Diels-Alder methodology with 1,1-binaphthalene-2,2-diol (BINOL) as a chiral inductor. By changing the chirality of the BINOL inductor, both enantiomeric forms of the resulting cycloadducts could be obtained with high enantioselectivities and yields. Simple chemical transformations of the cycloadducts gave two types of polyhydroxylated pipecolic acids. The synthetic strategy provides the first reported synthesis of chain-branched pipecolic acids.
TypeArticle
URIhttp://hdl.handle.net/1822/51348
DOI10.1055/s-0034-1378227
ISSN0936-5214
Peer-Reviewedyes
AccessRestricted access (Author)
Appears in Collections:CDQuim - Artigos (Papers)

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