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Title

Highly stereoselective synthesis of stereochemically defined polyhydroxylated propargylamines by alkynylation of n-benzylimines derived from (R)-glyceraldehyde.

AuthorsDíez, Roberto; Badorrey, Ramón CSIC ORCID; Díaz de Villegas, María D. CSIC ORCID; Gálvez, José A. CSIC ORCID
KeywordsAmino alcohols
Asymmetric synthesis
Diastereoselectivity
Schiff bases
Nucleophilic addition
Issue Date13-Mar-2007
PublisherWiley-VCH
CitationEuropean Journal of Organic Chemistry 2007(13): 2114 - 2120 (2007)
AbstractThe addition of the lithium derivative of tert-butyldimethylsilyl propargyl ether to N-benzylimines derived from (R)-2,3-O-isopropylideneglyceraldehyde has been achieved with acceptable yields and high diastereoselectivities. The syn/anti diastereoselectivity of the addition reaction can be controlled and reversed by the appropriate use of Lewis acids as imine precomplexing agents. Double stereodifferentiation processes using imines derived from (R)-2,3-O-isopropylideneglyceraldehyde and (R)- or (S)--methylbenzylamine as starting materials occur with total stereocontrol to afford syn and anti vic-propargylamino alcohol derivatives with orthogonally protected hydroxymethyl groups on both sides of the central core.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Description7 pages, 2 schemes, 1 figure1 1 table.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.200601011
URIhttp://hdl.handle.net/10261/19401
DOI10.1002/ejoc.200601011
Appears in Collections:(ICMA) Artículos

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