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1,2-Diastereoselective C–C Bond-Forming Reactions for the Synthesis of Chiral β-Branched α-Amino Acids

S N 2' sequences have been employed for the synthesis of β-branched α-amino acids using 1,2-diastereocontrol for forming C―C bonds. An oxazolidine fragment derived from Garner's aldehyde provides the handle for facial discrimination and acts as a masked amino acid functionality. This study encompasses directed and non-directed allylic substitution reactions. The stereocontrol of the oxazolidine appendage during terminal olefin hydroformylation was also studied. Efforts to understand the diastereochemical outcome of the reactions as well as synthetic applications are disclosed.