Synthesis of Highly Enantioenriched Chiral α-Aminoorganotins via Diastereoselective Ring Opening of Chiral <i>N</i>-(Arenesulfonyl) 2-Tributylstannyloxazolidines

trans-N-(Arenesulfonyl)-2-tributylstannyloxazolidines derived from (R)-phenylglycinol were diastereoselectively ring-opened by soft organometallic reagents in the presence of BF3·OEt2. Both higher order organocuprates and allyltributyltin afforded the desired products in good-to-excellent yields and high diastereoselectivities (dr up to 99/1). The stereochemical assignments of tributylstannyl-β-aminoalcohols were firmly established from NMR data and after determination of several radiocrystallographic structures. Mechanisms were proposed in order to rationalize the observed selectivities.