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

Upon transmetalation with n-butyllithium (THF, -78 degreesC, 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 (alpha-aminoalkyl)triorganostannanes whose absolute configuration of the major isomer was determined by an X-ray analysis.