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Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-chloro-1-nitrosocyclohexane as a practical [NH2+] equivalent

Published inHelvetica Chimica Acta, vol. 75, no. 6, p. 1965-1978
Publication date1992
Abstract

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq. HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5. These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S, S)-Isoleucine (17) and (S, S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate ‘amination' with 1.

Citation (ISO format)
VON OPPOLZER, Wolfgang, TAMURA, Osamu, DEERBERG, Joerg. Asymmetric Synthesis of α-Amino Acids and α-<i>N</i>-Hydroxyamino Acids from <i>N</i>-Acylbornane-10,2-sultams: 1-chloro-1-nitrosocyclohexane as a practical [NH<sub>2</sub><sup>+</sup>] equivalent. In: Helvetica Chimica Acta, 1992, vol. 75, n° 6, p. 1965–1978. doi: 10.1002/hlca.19920750622
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ISSN of the journal0018-019X
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