Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries

Yasuhiro Kawanami, Yoshio Ito, Toshiyuki Kitagawa, Yoshiyuki Taniguchi, Tsutomu Katsuki, Masaru Yamaguchi

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Abstract

trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable flexibility to substrates and reaction conditions.

Original languageEnglish
Pages (from-to)857-860
Number of pages4
JournalTetrahedron Letters
Volume25
Issue number8
DOIs
Publication statusPublished - Jan 1 1984

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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