Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl–Alkyl Cross-Coupling |
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Authors: | Xin Mu Yu Shibata Yusuke Makida Prof Gregory C Fu |
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Institution: | Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125 USA |
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Abstract: | Vicinal stereocenters are found in many natural and unnatural compounds. Although metal-catalyzed cross-coupling reactions of unactivated alkyl electrophiles are emerging as a powerful tool in organic synthesis, there have been virtually no reports of processes that generate, much less control, vicinal stereocenters. In this investigation, we establish that a chiral nickel catalyst can mediate doubly stereoconvergent alkyl–alkyl cross-coupling, specifically, reactions of a racemic pyrrolidine-derived nucleophile with cyclic alkyl halides (as mixtures of stereoisomers) to produce vicinal stereocenters with very good stereoselectivity. |
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Keywords: | Alkylierungen Asymmetrische Synthesen Kreuzkupplungen Nickel Zink |
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