Kinetic Resolution of Secondary Alcohols Catalyzed at the Exterior of Chiral Coordinated Capsules

Author:

Harada Kentaro1,Sekiya Ryo1ORCID,Haino Takeharu12ORCID

Affiliation:

1. Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University 1-3-1 Kagamiyama, Higashi-Hiroshima Hiroshima 739-8526 Japan

2. International Institute for Sustainability with Knotted Chiral Meta Matter (WPI-SKCM2) Hiroshima University 2-313 Kagamiyama, Higashi-Hiroshima Hiroshima 739-8527 Japan

Abstract

AbstractConfined spaces inside molecular hosts can function as reaction vessels. However, this concept significantly limits the scope of reactants. When the exterior of molecular hosts is used instead, we can ease the restriction because reactants are not necessary to be trapped inside molecular hosts, although studies along this line have not been reported. As a proof‐of‐concept of enantioselective reactions at the exterior of chiral molecular hosts, we utilized host‐guest complexes of enantiomerically enriched Cu‐coordinated capsules and guests possessing a catalytic center to realize the kinetic resolution of secondary alcohols. Under suitable reaction conditions, a selectivity factor of 2.6 was realized, demonstrating that the reactions occur at the exterior of the capsules. A series of experiments indicated that the substituents on the 2,2’‐bipyridyl arms and the alkyl chains on the lower rim contributed to the enantioselectivity of the reactions.

Funder

Japan Society for the Promotion of Science

JKA Foundation

Publisher

Wiley

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