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N-Boc-2-stannyloxazolidines Derived from (R)-Phenylgly- cinol: Preparation, Transmetalation, and Use as Precursors  of Enantioenriched (α-Aminoalkyl)triorganostannanes

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journal contribution
posted on 01.03.2004, 00:00 by Jean-Christophe Cintrat, Véronique Léat, Jean-Luc Parrain, Erwan Le Grognec, Isabelle Beaudet, Loïc Toupet, Jean-Paul Quintard
Upon transmetalation with n-butyllithium (THF, −78 °C, 30 min), 2-(triorganostannyl)oxazolidines afforded the corresponding 2-lithiooxazolidine species, which were proved to be configurationally stable under these experimental conditions. When 2-(triorganostannyl)oxazolidines were involved in reactions with organocuprates promoted by boron trifluoride, the oxazolidine ring was opened to give stereoselectively the enantioenriched N-Boc (α-aminoalkyl)triorganostannanes whose absolute configuration of the major isomer was determined by an X-ray analysis.