Abstract
Highly effective and stereoselective enamine-singlet oxygen coupling was achieved by synergistic chiral primary amine and photocatalysis in hexafluoroisopropanol. The current enamine catalysis enables α-hydroxylation of β-ketocarbonyls with good yields and high enantioselectivity across a broad range of substrates. Mechanistic studies revealed a direct participation of solvents in the critical enamine coupling step, and a solvent-1O2 H-bonding mode was invoked to account for the dramatic solvent effect.
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