Asymmetric Synthesis of α‐Allenylglycines

Medientyp: E-Artikel
Titel: Asymmetric Synthesis of α‐Allenylglycines
Beteiligte: Bucuroaia, Carmen; Groth, Ulrich; Huhn, Thomas; Klinge, Michael
Erschienen: Wiley, 2009
Erschienen in: European Journal of Organic Chemistry
Sprache: Englisch
DOI: 10.1002/ejoc.200900462
ISSN: 1434-193X; 1099-0690
Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
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Beschreibung: <jats:title>Abstract</jats:title><jats:p>The coupling of the homocuprate of the bislactim ether of <jats:italic>cyclo</jats:italic>‐(‐<jats:sc>L</jats:sc>‐Val‐Gly‐) (<jats:bold>9</jats:bold>) with primary propargyl halides produces the allenyl‐substituted bislactim ethers <jats:bold>11</jats:bold> in a highly diastereoselective manner, whereas the alkylation of the lithiated bislactim ether of <jats:italic>cyclo</jats:italic>‐(‐<jats:sc>L</jats:sc>‐Val‐Gly‐) yields the propargyl‐substituted bislactim ethers <jats:bold>12</jats:bold>. Subsequent hydrolysisaffords, after protection of the amino group, the methyl α‐allenylglycinates <jats:bold>15</jats:bold>, the α‐allenylglycines <jats:bold>16</jats:bold>, and the methyl α‐propargylglycinates <jats:bold>17</jats:bold>. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>

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