Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane

Article abstract of DOI:10.1016/S0040-4039(00)94411-3

Successive treatment of N-acylsultams 3 with NaN(TMS)₂, 1-chloro-1-nitrosocyclohexane (1) and 1N aq. HCl gave diastereomerically pure, crystalline N-hydroxyamino acid derivatives 4. Products 4 were converted to various amino acids 6, an N-BOC-amino acid 8 and to N-hydroxyamino acids 9. (S,S)-Isoleucine (16) was obtained from N-crotonoylsultam 13 via an organomagnesium-1,4-addition/enolate trapping process generating two stereogenic centers.