Asymmetric synthesis of orthogonally protected trans-cyclopropane c-amino acids via intramolecular ring closure
Date
2006
Authors
Fox, David J.
Pedersen, Daniel Sejer
Warren, Stuart
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Journal article
Citation
Organic and Biomolecular Chemistry, 2006; 4(16):3113-3116
Statement of Responsibility
David J. Fox, Daniel Sejer Pedersen and Stuart Warren
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Abstract
The synthesis of enantiomerically-enriched trans-cyclopropane amino- and hydroxy-acids can be achieved by intramolecular ring closure in moderate to good yields. The optically active cyclopropane precursors are easily prepared in a short sequence from inexpensive, commercially available olefins and tert-butyl acetate. Several leaving groups and bases were compared for the cyclopropanation step, showing that the diphenylphosphinate and tosyl leaving groups give the best results when used in combination with either LDA or NaHMDS.
School/Discipline
School of Chemistry and Physics : Chemistry
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© The Royal Society of Chemistry 2006