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Asymmetric Synthesis of α‐Allenylglycines
Author(s) -
Bucuroaia Carmen,
Groth Ulrich,
Huhn Thomas,
Klinge Michael
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900462
Subject(s) - chemistry , propargyl , ether , halide , alkylation , medicinal chemistry , organic chemistry , stereochemistry , catalysis
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)
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