Synthesis of Hydroxylated 1-Azabicyclohexane and Prolinol Derivatives by Stereo- and Regiocontrolled Staudinger Aminocyclization. Application to the Nonproteinogenic Amino Acid (2S,3S,4S)-3-Hydroxy-4-methylproline (HMP) and Its Enantiomer

Article abstract of DOI:10.1021/ja00201a033

On treatment with triphenylphosphine the azido epoxides 8/11 form enantio- and diastereomerically pure 1-azabicyclo<3.1.0>hexanes (9/12) via a Staudinger type aminocyclization reaction.Benzoic acid anhydride opens the aziridine ring in 9/12 to give prolin