150. Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane.
     Oppolzer, W.; Tamura, O.
     Tetrahedron Lett. 1990, 31, 991-994

Successive treatment of N-acylsultams 3 with NaN(TMS)₂, l-chloro-1-nitrosocyclohexane (1) and 1N aq. HCl gave diastereomerically pure, crystalline Nhydroxyamino acid derivatives 4. Products 4 were converted to various amino acids 6, an NBOC-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.

DOI : 10.1016/S0040-4039(00)94411-3 

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