Stereoselectivity in Cyclopropanation of Amino Acid-derived Enones
Stereoselectivity in Cyclopropanation of Amino Acid-derived Enones
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Date
2020-05-06
Authors
Kerns, Holli
Journal Title
Journal ISSN
Volume Title
Publisher
University Honors College Middle Tennessee State University
Abstract
An 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.
Description
Keywords
Basic and Applied Science,
Cyclopropanation,
amino acid,
quinine,
quinidine,
stereoselectivity,
catalyst