Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids |
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Authors: | Christopher W Barfoot Martin N Kenworthy Mahmood Ahmed |
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Institution: | a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK b GlaxoSmithKline, New Frontiers Science Park (North), Third Avenue, Harlow, Essex CM19 5AW, UK |
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Abstract: | Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues. |
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Keywords: | Cross-coupling α-Amino acids Organolithium Suzuki Alanine anions |
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