Asymmetric syntheses of β-phenylalanine, α-methyl-β-phenylalanines and derivatives
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 1153-1155
- https://doi.org/10.1039/c39930001153
Abstract
A strategy of highly stereoselective conjugate additions of lithium (R)-(α-methylbenzyl)benzylamide to tert-butyl cinnamate and its 2-methyl derivative combined with appropriate tandem or sequential electrophilic quenches allows the asymmetric syntheses of β-phenylalanine (95% enantiomeric excess) and homochiral (2R, 3S)- and (2S, 3S)-α-methyl-β-phenylalanine and the corresponding β-lactams (3R, 4S)- and (3S, 4S)-3-methyl-4-phenylazetidinones.Keywords
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