An efficient synthesis of cyclopropyl peptidomimetics has been developed in our laboratory, with the key step being the cyclopropanation of amino-acid derived enones to access both nitrocyclopropyl and estercyclopropyl peptidomimetics. However, the key cyclopropanation step suffers from a lack of stereoselectivity. Efforts to improve stereoselectivity in the cyclopropanation using quinine-based catalysts are reported here, with complete selectivity observed in some cases. In addition, efforts to improve the stereoselectivity in a subsequent ketone reduction are reported. The use of phenylalanine, leucine, isoleucine, valine, <i>t</i>-butyl glycine and proline as starting materials leads to the corresponding cyclopropyl peptidomimetics.<br/>

Improved stereoselectivity in the synthesis of cylopropyl peptidomimetics using quinine-based catalysts

255th National Meeting (2018)

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