Synthesis 2017; 49(02): 365-370
DOI: 10.1055/s-0036-1588898
paper
© Georg Thieme Verlag Stuttgart · New York

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

Keiji Mori
a   Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
b   Department 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
a   Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
,
Takahiko Akiyama*
a   Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
› Author Affiliations
Further Information

Publication History

Received: 02 August 2016

Accepted after revision: 17 September 2016

Publication Date:
14 October 2016 (online)


Dedicated to Professor Dieter Enders for his 70th 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.

Supporting Information

 
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