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

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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