A Tunable and Enantioselective Hetero-Diels-Alder Reaction Provides Access to Distinct Piperidinoyl Spirooxindoles

Angewandte Chemie
Samydurai JayakumarKamal Kumar

Abstract

The active complexes of chiral N,N'-dioxide ligands with dysprosium and magnesium salts catalyze the hetero-Diels-Alder reaction between 2-aza-3-silyloxy-butadienes and alkylidene oxindoles to selectively form 3,3'- and 3,4'-piperidinoyl spirooxindoles, respectively, in very high yields and with excellent enantioselectivities. The exo-selective asymmetric cycloaddition successfully regaled the construction of sp3 -rich and highly substituted natural-product-based spirooxindoles supporting many chiral centers, including contiguous all-carbon quaternary centers.

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Citations

Nov 27, 2019·Chemistry : a European Journal·Monika KořenkováLibor Dostál
May 18, 2018·Chemical Communications : Chem Comm·Guang-Jian Mei, Feng Shi
Jun 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Boris LetribotValérie Thiéry
Jan 19, 2021·Angewandte Chemie·Tobias WagenerFrank Glorius

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