☆ 4.5 Article

Asymmetric Synthesis of α-Allenylglycines

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2009)

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume 2009, Issue 21, Pages 3605-3612

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.200900462

Keywords

Asymmetric synthesis; Amino acids; Cuprates; Allenes; Alkynes

Categories

Chemistry, Organic

Funding

Herbert Quandt Foundation

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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 hydrolysis affords, after protection of the amino group, the methyl alpha-allenylglycinates 15, the alpha-allenylglycines 16, and the methyl alpha-propargylglycinates 17. ((C) Wiley-VCH Verlag GmbH & Co. KGdA, 69451 Weinheim, Germany, 2009)

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