Memory of Chirality : Alkylation of α-Amino Acid Derivatives

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Author(s)

Abstract

<I>N</I>-Boc-<I>N</I>-MOM-α-amino acid derivatives (Phe, Val, Leu, His, Trp, Tyr, Dopa) underwent asymmetric α-methylation in 76-93% ee by treatment with KHMDS followed by methyl iodide in the absence of any external chiral source. A chiral nonracemic enolate with dynamic axial chirality is proposed as the crucial intermediate whose racemization barrier is 16.0 kcal/mol and the corresponding half-life is 22h at -78°C.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(11), 1095-1099, 2000-11-01

    The Society of Synthetic Organic Chemistry, Japan

References:  27

Cited by:  2

Codes

  • NII Article ID (NAID)
    10008822326
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    5549733
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  CJPref  NDL  J-STAGE 
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