A diastereoselective preparation of cyclic α-aminoboronates
John Kim1, Anna Page1, Ryan T Vanderlinden1
1Department of Chemistry, University of Utah, Rm 2020, Salt Lake City UT 84112.
Abstract:
Chiral α-amino- and α-amidoboronates are established pharmacophores in numerous drugs and drug candidates, however, methods to prepare this motif are limited. We report the preparation of cyclic α-amino boronates via a three-component coupling reaction of salicylaldehydes, tetrahydroxydiboron, and chiral amines. Deploying 1,2-aminoalcohol and aminoacid derivatives delivers a structurally diverse set of cyclic α-aminoboronates. Moderate to high diastereoselectivity is noted both at the newly forged carbon-boron bond and at the tetrahedral boron center.
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