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Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization
Author(s) -
Miller Zachary D.,
Lee Byung Joo,
Yoon Tehshik P.
Publication year - 2017
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.201706975
Subject(s) - cyclobutanes , enantioselective synthesis , chemistry , cyclobutane , lewis acids and bases , catalysis , styrene , cycloaddition , chiral lewis acid , combinatorial chemistry , organic chemistry , photochemistry , stereochemistry , copolymer , ring (chemistry) , polymer
The synthesis of unsymmetrical cyclobutanes by controlled heterodimerization of olefins remains a substantial challenge, particularly in an enantiocontrolled fashion. Shown herein is that chiral Lewis acid catalyzed triplet sensitization enables the synthesis of highly enantioenriched diarylcyclobutanes by photocycloaddition of structurally varied 2′‐hydroxychalcones with a range of styrene coupling partners. The utility of this reaction is demonstrated through the direct synthesis of a representative norlignan cyclobutane natural product.