Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones

Zhi‐Min Chen, Qing‐Wei Zhang, Zhihua Chen, Hui Li, Yong‐Qiang Tu, Fu‐Min Zhang, Jin‐Miao Tian

Journal of the American Chemical Society · 2011 · 178 citations · 51 references

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Abstract

A novel asymmetric halogenation/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. Two types of β-haloketones (X = Br, Cl) were obtained with up to 95% yield and 99% enantiomeric excess. The desired (+) and (-) enantiomers of the β-haloketones were readily obtained.

References

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