In this study, we present the synthesis of new, stereodefined allylboronic acids employed to investigate the stereochemistry of the Cu-catalyzed cross-coupling of allylboronic acids with α-diazoketones. According to our results, this reaction proceeds with retention of the relative configuration of the allylboronic acid substrate. We suggest that the stereoinduction step involves a syn S2'-type transmetalation of the allylboronic acid substrate with a Cu-carbene species.
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| http://dx.doi.org/10.1021/acs.orglett.7b00433 | DOI Listing |
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