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Catalytic Enantioselective Formal (4+2) Cycloaddition by Aldol–Aldol Annulation of Pyruvate Derivatives with Cyclohexane‐1,3‐Diones to Afford Functionalized Decalins
Author(s) -
Chouthaiwale Pandurang V.,
Aher Ravindra D.,
Tanaka Fujie
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.201808219
Subject(s) - enantioselective synthesis , aldol reaction , decalin , stereocenter , chemistry , cycloaddition , organocatalysis , annulation , cyclohexane , catalysis , cycloalkane , organic chemistry , combinatorial chemistry
The decalin structure is found in bioactive molecules. We have developed catalytic enantioselective formal (4+2) cycloaddition reactions via aldol–aldol cascade reactions between pyruvate‐derived diketoester derivatives and cyclohexane‐1,3‐dione derivatives that afford highly functionalized decalin derivatives. The reactions were performed using a quinidine‐derived catalyst under mild conditions. Decalin derivatives bearing up to six chiral carbon centers including tetrasubstituted carbon centers were synthesized with high diastereo‐ and enantioselectivities. Five to six stereogenic centers were generated from achiral molecules with the formation of two C−C bonds in a single transformation resulting in the formation of the decalin system.