Enantioselective Catalysis of the Intermolecular [2+2] Photocycloaddition between 2‐Pyridones and Acetylenedicarboxylates | Zendy

Maturi Mark M. | Zendy; Bach Thorsten | Zendy

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Enantioselective Catalysis of the Intermolecular [2+2] Photocycloaddition between 2‐Pyridones and Acetylenedicarboxylates

Author(s) -

Maturi Mark M.,

Bach Thorsten

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201403885

Subject(s) - enantioselective synthesis , intermolecular force , catalysis , substrate (aquarium) , chemistry , non covalent interactions , combinatorial chemistry , hydrogen bond , photochemistry , computational chemistry , organic chemistry , molecule , geology , oceanography

Intermolecular [2+2] photocycloadditions represent the most versatile and widely applicable of photochemical reactions. For the first time, such intermolecular reactions have been carried out in a catalytic fashion using a chiral triplet sensitizer, with high enantioselectivity (up to 92 % ee ). The low catalyst loading (2.5–5 mol %) underlines the high efficiency of the process both in terms of reaction acceleration and differentiation of the enantiotopic faces of the substrate. The substrate is anchored to the chiral catalyst through noncovalent interactions (hydrogen bonds), thus providing a chiral environment in which the enantioselective photocycloaddition proceeds. The densely functionalized products present numerous possibilities for further synthetic transformations.

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