Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary. © 2005 Elsevier Ltd. All rights reserved.
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Kotake, T., Hayashi, Y., Rajesh, S., Mukai, Y., Takiguchi, Y., Kimura, T., & Kiso, Y. (2005). Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions. Tetrahedron, 61(15), 3819–3833. https://doi.org/10.1016/j.tet.2005.01.135