Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes
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Author(s)
Wang, Yiming
Buchwald, Stephen Leffler
Date Issued
April 2016
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Wang, Yi-Ming, and Buchwald, Stephen L. “Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes.” Journal of the American Chemical Society 138, 15 (April 2016): 5024–5027 © 2016 American Chemical Society
Version
Final published version
Abstract
The creation of configurationally well-defined stereogenic centers during the course of carbon–carbon bond formation is of great importance for the synthesis of complex organic molecules. Due to the synthetic versatility of the olefin functional group, the enantioselective installation of an allylic fragment has long been regarded as a particularly valuable subset of stereoselective C–C bond-forming transformations.(1-3) Among the numerous transition-metal-catalyzed methods for enantioselective allylation, the copper-catalyzed addition of organometallic reagents to allylic electrophiles is distinguished by its applicability to non-heteroatom-stabilized carbon nucleophiles.(4) As a consequence, these methods can be readily applied to the construction of C–C bonds remote from polar functional groups in an enantioselective manner, a process for which few other catalytic methods are available. In typical copper-catalyzed allylic substitution reactions, the organocopper intermediate undergoes addition to a prochiral allylic electrophile, resulting in the formation of a stereocenter α to a double bond. In contrast, the addition of an α-chiral organocopper species to an allylic electrophile to furnish a β-stereocenter has seldom been reported and would represent a significant advance (Figure 1A).(5)
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.6B02527
