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Scientific article
Letter
English

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

Published inTetrahedron Letters, vol. 31, no. 7, p. 991-994
Publication date1990
Abstract

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.

Citation (ISO format)
VON OPPOLZER, Wolfgang, TAMURA, Osamu. Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane. In: Tetrahedron Letters, 1990, vol. 31, n° 7, p. 991–994. doi: 10.1016/S0040-4039(00)94411-3
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ISSN of the journal0040-4039
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