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Highly stereoselective synthesis of stereochemically defined polyhydroxylated propargylamines by alkynylation of n-benzylimines derived from (R)-glyceraldehyde.
|Authors:||Díez, Roberto; Badorrey, Ramón CSIC ORCID; Díaz de Villegas, María D. CSIC ORCID; Gálvez, José A. CSIC ORCID||Keywords:||Amino alcohols
|Issue Date:||13-Mar-2007||Publisher:||Wiley-VCH||Citation:||European Journal of Organic Chemistry 2007(13): 2114 - 2120 (2007)||Abstract:||The 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)||Description:||7 pages, 2 schemes, 1 figure1 1 table.||Publisher version (URL):||http://dx.doi.org/10.1002/ejoc.200601011||URI:||http://hdl.handle.net/10261/19401||DOI:||10.1002/ejoc.200601011|
|Appears in Collections:||(ICMA) Artículos|
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