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Asymmetric Synthesis of Dihydropyranones via Gold(I)‐Catalyzed Intermolecular [4+2] Annulation of Propiolates and Alkenes
Author(s) -
Kim Hanbyul,
Choi Su Yeon,
Shin Seunghoon
Publication year - 2018
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.201807514
Subject(s) - annulation , enantioselective synthesis , chemistry , intermolecular force , catalysis , carbene , alkyne , combinatorial chemistry , solvent , selectivity , medicinal chemistry , organic chemistry , molecule
Intermolecular asymmetric gold catalysis involving alkyne activation presents a significant challenge due to its distinct mechanistic mode from other metals. Herein, we report a highly enantioselective synthesis of α,β‐unsaturated δ‐lactones from [4+2] annulation of propiolates and alkenes in upto 95 % ee . Notably, for the desired chiral recognition, the choice of 1,1,2,2‐tetrachloroethane as solvent was found to be crucial. Furthermore, an anionic surfactant (sodium dodecyl sulfate) improved the product selectivity in the divergence of the cyclopropyl gold carbene intermediate.