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Morita, Taiki; Murakami, Hiroki; Asawa, Yasunobu; Nakamura, Hiroyuki
Angewandte Chemie International Edition, February 7, 2022, Volume: 61, Issue: 7Journal Article
A palladium‐catalyzed N−H/B−H double activation of 1,2‐dihydro‐1,2‐benzazaborines proceeded via cycloaddition with vinyl ethylene carbonate to produce polycyclic oxazaborolidines in 31–96 % yield. The key step in this process is the release of molecular hydrogen from a borate intermediate. Using a SPINOL‐derived phosphoramidite as a chiral ligand, chiral oxazaborolidines were synthesized in good to high yields with excellent enantioselectivity (up to 95 % ee). The vinyl group of the resulting oxazaborolidine underwent metathesis, Heck reaction, and Wacker oxidation without affecting the oxazaborolidine framework. Catalytic N−H/B−H double activation of 1,2‐azaborines has been demonstrated. A wide variety of 1,2‐azaborines underwent cycloaddition with vinylethylene carbonate through N−H/B−H bond cleavage to produce unique polycyclic oxazaborolidines under mild conditions. Furthermore, highly enantioselective direct functionalization of 1,2‐azaborines afforded chiral tricyclic oxazaborolidines.
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