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

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

doi:https://doi.org/10.1016/S0957-4166(99)00457-7

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

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-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 language	English
Pages (from-to)	4211-4224
Journal	Tetrahedron Asymmetry
Volume	10
DOIs	https://doi.org/10.1016/S0957-4166(99)00457-7
Publication status	Published - 29 Oct 1999

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title = "Asymmetric synthesis of quaternary α-amino acids using D-ribonolactone acetonide as chiral auxiliary",

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.",

author = "Marcial Moreno-Ma{\~n}as and Elisenda Trepat and Sebasti{\'a}n, {Rosa M.} and Adelina Vallribera",

year = "1999",

month = oct,

day = "29",

doi = "https://doi.org/10.1016/S0957-4166(99)00457-7",

language = "English",

volume = "10",

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T1 - Asymmetric synthesis of quaternary α-amino acids using D-ribonolactone acetonide as chiral auxiliary

AU - Moreno-Mañas, Marcial

AU - Trepat, Elisenda

AU - Sebastián, Rosa M.

AU - Vallribera, Adelina

PY - 1999/10/29

Y1 - 1999/10/29

N2 - 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.

AB - 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.

U2 - https://doi.org/10.1016/S0957-4166(99)00457-7

DO - https://doi.org/10.1016/S0957-4166(99)00457-7

M3 - Article

VL - 10

SP - 4211

EP - 4224

ER -