Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide | Zendy

Tadashi Ema | Zendy; Maki Yokoyama | Zendy; Sagiri Watanabe | Zendy; Sota Sasaki | Zendy; Hiromi Ota | Zendy; Kazuto Takaishi | Zendy

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Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

Author(s) -

Tadashi Ema,

Maki Yokoyama,

Sagiri Watanabe,

Sota Sasaki,

Hiromi Ota,

Kazuto Takaishi

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01838

Subject(s) - enantioselective synthesis , chemistry , kinetic resolution , catalysis , hydrogen bond , epoxide , trifluoromethyl , substituent , combinatorial chemistry , organic chemistry , stereochemistry , molecule , alkyl

Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO 2 . The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

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