Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation

Keiji Mori; Hiroki Kishi; Takahiko Akiyama

doi:10.1055/s-0036-1588898

Synthesis, Table of Contents

Synthesis 2017; 49(02): 365-370
DOI: 10.1055/s-0036-1588898

paper

Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation

Keiji Mori

^aDepartment of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan

^bDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho, Koganei, Tokyo 184-8588, Japan Email: takahiko.akiyama@gakushuin.ac.jp

,

Hiroki Kishi

^aDepartment of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan

,

Takahiko Akiyama*

^aDepartment of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan

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Abstract

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Dedicated to Professor Dieter Enders for his 70^th birthday

Abstract

We report herein a highly efficient kinetic resolution of PHANOL by chiral phosphoric acid catalyzed asymmetric acylation. PHANOL enantiomers were well differentiated by the chiral environment of chiral phosphoric acid, and both the corresponding monoester and PHANOL were obtained with excellent enantioselectivities (98% ee and 92% ee, respectively). Detailed examination of the substrates suggests that the presence of two hydroxy groups in PHANOL was critical for both reactivity and enantioselectivity.

Key words

asymmetric synthesis - chiral biaryl - asymmetric acylation - kinetic resolution - chiral phosphoric acid

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References

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