ol7b00433_si_001.pdf (1.12 MB)
Copper-Catalyzed, Stereoselective Cross-Coupling of Cyclic Allyl Boronic Acids with α‑Diazoketones
journal contribution
posted on 2017-03-23, 20:13 authored by Dong Wang, Kálmán J. SzabóIn
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 SE2′-type transmetalation of the allylboronic acid substrate
with a Cu–carbene species.