Asymmetric Synthesis of α‐Amino Acids and α‐N‐Hydroxyamino Acids from N‐Acylbornane‐10,2‐sultams: 1‐chloro‐1‐nitrosocyclohexane as a practical [NH] equivalent
- 2 October 1992
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 75 (6) , 1965-1978
- https://doi.org/10.1002/hlca.19920750622
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.Keywords
This publication has 51 references indexed in Scilit:
- Enantioselective synthesis of (+)-3-isorauniticine via a catalytic tandem palladium-ene/carbonylation reactionJournal of the American Chemical Society, 1991
- Stereoselektive Aromatenalkylierung mit Threonin‐trifluormethansulfonatenEuropean Journal of Inorganic Chemistry, 1988
- Enantioselective Synthesis of β‐Necrodol and of 1‐Epi‐β‐necrodol via Asymmetric 1,4‐Addition and Magnesium‐Ene Cyclization. Preliminary CommunicationHelvetica Chimica Acta, 1986
- Diastereoselectivity and Reactivity in the Diels‐Alder Reactions of α‐Chloronitroso EthersHelvetica Chimica Acta, 1986
- Ene reactions with α‐chloronitroso compounds: Asymmetric synthesis of N‐allylhydroxylaminesRecueil des Travaux Chimiques des Pays-Bas, 1986
- C -Nitroso compounds. Part XXXVII. The reactivity of α-chloronitroso compounds towards organoaluminium reagentsRecueil des Travaux Chimiques des Pays-Bas, 1986
- Heliflex chirasil-Val; GC of amino acid enantiomersJournal of High Resolution Chromatography, 1983
- C‐Nitroso compounds. Part XXXIV. Reaction of α‐chloronitroso compounds with methyl and phenyl Grignard reagents. A convenient synthesis of α,α‐dialkyl‐N‐methyl and ‐N‐phenyl nitronesRecueil des Travaux Chimiques des Pays-Bas, 1980
- Synthesis of (S,S)-2-Amino-3-phenylbutyric AcidBulletin of the Chemical Society of Japan, 1979
- The Biogenesis of Nicotine. III. Further Observations on the Incorporation of Ornithine into the Pyrrolidine Ring1Journal of the American Chemical Society, 1957