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Coeffard, V., Le Grognec, E., Beaudet, I., Evain, M. & Quintard, J.-P. (2009) Synthesis of Highly Enantioenriched Chiral alpha-Aminoorganotins via Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl) 2-Tributylstannyloxazolidines. J. Org. Chem. 74 5822–5838.
Added by: Laurent Cournède (2016-03-10 21:41:23) |
| Type de référence: Article DOI: 10.1021/jo900223k Numéro d'identification (ISBN etc.): 0022-3263 Clé BibTeX: Coeffard2009 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: acyclic stereoselection, amino-alcohols, asymmetric-synthesis, configurational stability, dipole-stabilized anions, dynamic kinetic resolution, enantioselective lithiation-substitution, hydroxy aldehydes, organometallic reagents, tin-lithium exchange Créateurs: Beaudet, Coeffard, Evain, Le Grognec, Quintard Collection: J. Org. Chem. |
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| Résumé |
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trans-N-(Arenesulfonyl)-2-tributylstannyloxazolidines derived from (R)-phenylglycinol were diaster-ecoselectively ring-opened by soft organometallic reagents in the presence of BF(3)center dot OEt(2). Both higher order organocuprates and allyltributyltin afforded the desired products in good-to-excellent yields and high diasterecoseloctivities (dr tip to 99/1). The stercochemical assignments of tributylstannyl-beta-aminoalcohols were firmly established from NMR data and after determination of several radiocrystallographic structures. Mechanisms were proposed in order to rationalize the observed selectivities.
Added by: Laurent Cournède |