Chiral copper-catalyzed asymmetric monoarylation of vicinal diols with diaryliodonium salts

The copper-catalyzed enantioselective monoarylation of meso-1,2-diols by the use of diaryliodonium triflates as aryl sources has been developed. The chiral copper(II) complex catalyzed the asymmetric desymmetrization effectively to afford optically active β-aryloxy alcohols in moderate to high chemical yields and enantioselectivity.

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(R,R)-(+)-2,2′-(Nonane-5,5-diyl)bis(4-phenyl-2-oxazoline)C27H34N2O2[α]D27 = +69.1 (c 0.64, CH2Cl2)Source of chirality: amino acidAbsolute configuration: (R,R)

(1S,2R)-(−)-2-PhenoxycycloheptanolC13H18O2Ee: 59%[α]D26 = −8.3 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R)

(1S,2R)-(−)-2-PhenoxycyclohexanolC12H16O2Ee: 24%[α]D25 = −9.6 (c 0.75, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R)

(2S,3R)-(−)-3-Phenoxybutan-2-olC10H14O2Ee: 37%[α]D27 = −11.2 (c 1.23, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3R)