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Helical Multi-Coordination Anion-Binding Catalysts for the Highly Enantioselective Dearomatization of Pyrylium Derivatives.

ABSTRACT: A general and highly enantioselective synthesis of oxygen heterocycles from readily available in?situ generated pyrylium derivatives has been realized by embracing a multi-coordination approach with helical anion-binding tetrakistriazole catalysts. The high activity of the tetrakistriazole (TetraTri) catalysts, with distinct confined anion-binding pockets, allows for remarkably low catalyst loadings (down to 0.05?mol?%), while providing a simple access to chiral chromanones and dihydropyrones in high enantioselectivities (up to 98:2 e.r.). Moreover, experimental and theoretical studies provide new insights into the hydrogen-donor ability and key binding interactions of the TetraTri catalysts and its host:guest complexes, suggesting the formation of a 1:3 species.

SUBMITTER: Fischer T

PROVIDER: S-EPMC6470695 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Helical Multi-Coordination Anion-Binding Catalysts for the Highly Enantioselective Dearomatization of Pyrylium Derivatives.

Fischer Theresa T Bamberger Julia J Gómez-Martínez Melania M Piekarski Dariusz G DG García Mancheño Olga O

Angewandte Chemie (International ed. in English) 20181213 10

A general and highly enantioselective synthesis of oxygen heterocycles from readily available in situ generated pyrylium derivatives has been realized by embracing a multi-coordination approach with helical anion-binding tetrakistriazole catalysts. The high activity of the tetrakistriazole (TetraTri) catalysts, with distinct confined anion-binding pockets, allows for remarkably low catalyst loadings (down to 0.05 mol %), while providing a simple access to chiral chromanones and dihydropyrones in ...[more]

PMID: 30427107

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