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Volumn 31, Issue 7, 1990, Pages 991-994

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

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; HYDROXYAMINO ACID;

EID: 0025191224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)94411-3     Document Type: Article
Times cited : (135)

References (48)
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    • Preparation of 1:
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    • 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 nitrones
    • Reactions of nitroso chloride 1 with organ omagnesium and aluminum reagents were described to give variable mounts of nitrone products:
    • (1980) Recueil des Travaux Chimiques des Pays-Bas , vol.99 , pp. 278
    • Schenk1    Beekes2    van der Drift3    de Boer4
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    • 1HNMR and MS or elemental analysis. No sharp melting points were observed due to decomposition.
  • 39
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    • W. Oppolzer, J. Biagg, I. Rodriguez, E. Walther, J. Am. Chem. Soc. in press;
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    • W. Oppolzer, C. Starkemann, J. Blagg, unpublished;
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    • Enantioselective Synthesis of ?-Necrodol and of 1-Epi-?-necrodolvia Asymmetric 1,4-Addition and Magnesium-Ene Cyclization. Preliminary Communication
    • (1986) Helvetica Chimica Acta , vol.69 , pp. 1817
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    • Asymmetric Induction on Copper(I) Chloride catalyzed 1,4-addition of alkylmagnesium chlorides to ?, ?-disubstituted (E)-enoylsultams and subsequent protonation
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    • Based on previous work, it was expected that addition of EtMgBr to 13 generates a chelated (Z)-magnesium enolate possessing the (S)-configuration at C(β). This intermediate resembles the enantiomer of 10 undergoing analogous electrophilic attack from the face opposite to the lone electron pair at the nitrogen atom.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.