Synthesis of β-Silyl α-Amino Acids via Visible-Light-Mediated Hydrosilylation
Yi Wan, Jia-Jie Zhu, Qiyang Yuan, Wei Wang, Yongqiang Zhang
Abstract
An expedient synthesis of β-silyl α-amino acids is reported via the application of visible-light-mediated hydrosilylation. The reaction utilizes readily accessible and structurally diverse hydrosilanes to provide radicals for conjugate addition to dehydroalanine ester and analogues. Notably, the use of chiral methyleneoxazolidinone as the substrate and chiral inducer enabled the highly stereoselective synthesis. Furthermore, the reaction could also be performed in a continuous flow fashion and scaled up to the gram scale.
Topics & Concepts
HydrosilylationChemistrySilylationConjugateStereoselectivitySubstrate (aquarium)DehydroalanineRadicalTartaric acidCombinatorial chemistryAmino acidStereochemistryOrganic chemistryCatalysisBiochemistryMathematical analysisOceanographyMathematicsCitric acidGeologyRadical Photochemical ReactionsOrganoboron and organosilicon chemistrySulfur-Based Synthesis Techniques