(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative:: practical asymmetric synthesis of α-amino acids
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Guillena, G
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Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, SpainUniv Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
Guillena, G
[1
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Nájera, C
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Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, SpainUniv Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
The lithium enolate of enantiomerically pure N-[bis(methylthio)methylene] glycinate 11 derived from (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one reacts with alkyl halides giving the alkylated derivatives 12 with a high degree of control of the diastereoselectivity. These alkylated systems are easily hydrolyzed to the corresponding cx-amino acids, the chiral auxiliary being recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.