Publication: A New General Approach to Enantiomerically Pure Cyclic and Open-Chain (R) - and (S)-alpha,alpha-Disubstituted alpha-Amino Acids
A New General Approach to Enantiomerically Pure Cyclic and Open-Chain (R) - and (S)-alpha,alpha-Disubstituted alpha-Amino Acids
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Obrecht, D., Spiegler, C., Schönholzer, P., Müller, K., Heimgartner, H., & Stierli, F. (1992). A New General Approach to Enantiomerically Pure Cyclic and Open-Chain (R) - and (S)-alpha,alpha-Disubstituted alpha-Amino Acids. Helvetica Chimica Acta, 75, 1666–1696. https://doi.org/10.1002/hlca.19920750522
Abstract
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Abstract
A wide range of cyclic and open-chain alpa,alpha-disubstituted alpha-amino acids 1a-p were prepared. The racemic N-acylated alpha,alpha-disubstituted amino acids were resolved by coupling to chiral amines 15-18 derived from (S)- phenylalanine to form diastereoisomers 19/20 or 21/22 that could be separated by crystallization and/or flash chromatography on silica gel (Scheme 3). Selective cleavage via the 1,3-oxazol-5(4H)-ones 10a-p gave the corresponding optically pure alpha,alpha-disubstituted amino-acid derivatives 11 or 12 in high y
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- Obrecht, Daniel
- Spiegler, Clive
- Schönholzer, Peter
- Müller, Klaus
- Heimgartner, Heinz
- Stierli, Friedrich
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Obrecht, D., Spiegler, C., Schönholzer, P., Müller, K., Heimgartner, H., & Stierli, F. (1992). A New General Approach to Enantiomerically Pure Cyclic and Open-Chain (R) - and (S)-alpha,alpha-Disubstituted alpha-Amino Acids. Helvetica Chimica Acta, 75, 1666–1696. https://doi.org/10.1002/hlca.19920750522
