Highly Enantioselective Synthesis of β‐Aminophosphinates with Two Stereogenic Atoms and Their Conversion into Optically Pure Ethyl β‐Amino‐H‐phosphinates
State Key Laboratory of Bio‐organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng‐lin Road, Shanghai, 200032 (China), Fax: (+86)?21‐5492‐5379
Abstract:
β‐Amino acid analogues : The nucleophilic addition of ethyl (diethoxyethyl)methylphosphinate to a variety of (S)‐(tert‐butanesulfinyl)imines leads to the isolation of two enantioenriched β‐aminophosphinates (>95 % ee; see scheme). Subsequent removal of the protecting groups through pivotal metal‐catalyzed thiophenolysis leads to optically pure ethyl β‐amino‐H‐phosphinates.
