Stereoselectivity in Cyclopropanation of Amino Acid-derived Enones

dc.contributor.authorKerns, Holli
dc.date.accessioned2020-06-08T17:13:36Z
dc.date.available2020-06-08T17:13:36Z
dc.date.issued2020-05-06
dc.description.abstractAn efficient synthesis of cyclopropyl peptidomimetics was developed by Dunlap et. al.; the key step of this synthesis is 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. The goal of this study is to improve stereoselectivity in the cyclopropanation step using Gaunt's quinine and quinidine-based catalysts. Prior work using Gaunt's quinine methyl ether catalyst has shown improved diastereoselectivity for the syn isomer of some amino acids. Current efforts to improve diastereoselectivity using Gaunt's quinine and quinidine benzyl ether catalysts are reported here. The catalysts are selective for opposing diastereomers and improve diastereoselectivity for a wider range of amino acids.en_US
dc.identifier.urihttps://jewlscholar.mtsu.edu/handle/mtsu/6243
dc.language.isoen_USen_US
dc.publisherUniversity Honors College Middle Tennessee State Universityen_US
dc.subjectBasic and Applied Scienceen_US
dc.subjectCyclopropanationen_US
dc.subjectamino aciden_US
dc.subjectquinineen_US
dc.subjectquinidineen_US
dc.subjectstereoselectivityen_US
dc.subjectcatalysten_US
dc.titleStereoselectivity in Cyclopropanation of Amino Acid-derived Enonesen_US
dc.typeThesisen_US

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