Asymmetric synthesis of quaternary α-amino acids using D-ribonolactone acetonide as chiral auxiliary

Marcial Moreno-Mañas, Elisenda Trepat, Rosa M. Sebastián, Adelina Vallribera

Research output: Contribution to journalArticleResearchpeer-review

22 Citations (Scopus)

Abstract

We describe a new simple methodology to prepare enantiopure α,α- dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure α-methyl and α-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of α,α-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4- disubstituted 3-methyl-2-pyrazolin-5-ones.
Original languageEnglish
Pages (from-to)4211-4224
JournalTetrahedron Asymmetry
Volume10
DOIs
Publication statusPublished - 29 Oct 1999

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