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Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles.
J Org Chem. 2015 Jul 02; 80(13):6864-9.JO

Abstract

A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Netz I
Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
Kucukdisli M
Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
Opatz T
Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.

MeSH

AlkylationAmino AcidsCatalysisDioxanesMolecular StructureNitrilesProtonsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

26024300

Citation

Netz, Isabelle, et al. "Enantioselective Synthesis of α-Quaternary Amino Acids By Alkylation of Deprotonated Α-Aminonitriles." The Journal of Organic Chemistry, vol. 80, no. 13, 2015, pp. 6864-9.
Netz I, Kucukdisli M, Opatz T. Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles. J Org Chem. 2015;80(13):6864-9.
Netz, I., Kucukdisli, M., & Opatz, T. (2015). Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles. The Journal of Organic Chemistry, 80(13), 6864-9. https://doi.org/10.1021/acs.joc.5b00868
Netz I, Kucukdisli M, Opatz T. Enantioselective Synthesis of α-Quaternary Amino Acids By Alkylation of Deprotonated Α-Aminonitriles. J Org Chem. 2015 Jul 2;80(13):6864-9. PubMed PMID: 26024300.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles. AU - Netz,Isabelle, AU - Kucukdisli,Murat, AU - Opatz,Till, Y1 - 2015/06/12/ PY - 2015/5/30/entrez PY - 2015/5/30/pubmed PY - 2016/2/19/medline SP - 6864 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 13 N2 - A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/26024300/Enantioselective_Synthesis_of_α_Quaternary_Amino_Acids_by_Alkylation_of_Deprotonated_α_Aminonitriles_ DB - PRIME DP - Unbound Medicine ER -