Asymmetric Synthesis of α‐Allenylglycines
Open Access
- 6 July 2009
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2009 (21) , 3605-3612
Abstract
The coupling of the homocuprate of the bislactim ether of cyclo‐(‐L‐Val‐Gly‐) (9) with primary propargyl halides produces the allenyl‐substituted bislactim ethers 11 in a highly diastereoselective manner, whereas the alkylation of the lithiated bislactim ether of cyclo‐(‐L‐Val‐Gly‐) yields the propargyl‐substituted bislactim ethers 12. Subsequent hydrolysisaffords, after protection of the amino group, the methyl α‐allenylglycinates 15, the α‐allenylglycines 16, and the methyl α‐propargylglycinates 17. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)Keywords
This publication has 27 references indexed in Scilit:
- α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanismsTetrahedron: Asymmetry, 2006
- Efficient Synthesis ofβ,γ-Alkynylα-Amino Acid Derivatives by Ag(Ι)-Catalyzed Alkynylation ofα-Imino EstersAdvanced Synthesis & Catalysis, 2004
- General synthesis of .beta.,.gamma.-alkynylglycine derivativesThe Journal of Organic Chemistry, 1990
- Synthesis of α-amino acids with β,γ-unsaturated side chainsTetrahedron, 1987
- Stereoselective synthesis of β,γ-unsaturated amino acidsPure and Applied Chemistry, 1987
- Allenic suicide substrates. New inhibitors of vitamin B6 linked decarboxylasesJournal of the American Chemical Society, 1984
- Suicide substrates: mechanism-based enzyme inactivatorsTetrahedron, 1982
- Asymmetric Syntheses via Heterocyclic Intermediates; XIII1. Enantioselective Synthesis of (R)-α-Alkenylalanine Methyl Esters using L-Valine as Chiral Auxiliary ReagentSynthesis, 1982
- Enantioselektive Synthese von (R)-α-VinylaminosäurenAngewandte Chemie, 1981
- Synthesis and Resolution of Vinylglycine, a beta,gamma-Unsaturated alpha-Amino Acid.Acta Chemica Scandinavica, 1974