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- W4367173673 endingPage "6524" @default.
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- W4367173673 abstract "The synthesis of chiral α-monosubstituted-ß-dicarbonyls is a challenging task in asymmetric catalysis due to the rapid, typically uncontrolled, product racemization or epimerization under most reaction conditions. For this reason, diastereoselective additions of unsubstituted ß-dicarbonyls to π-electrophiles are unusual. Herein, we disclose a simple catalytic crystallization-driven enantio- and diastereoselective Mannich reaction for the synthesis of stereodefined α-monosubstituted-ß-keto esters, dissymmetric ß-diesters, dissymmetric ß-diketones, and ß-keto amides that productively leverages product epimerization in solution. Mechanistic studies suggest a scenario where the initial enantioselective, diastereodivergent skeletal assembly is catalyzed by a chiral tertiary amine organocatalyst, which then facilitates second stage crystallization-induced diastereoconvergence to provide the challenging α-stereocenter in excellent stereoselectivity." @default.
- W4367173673 created "2023-04-28" @default.
- W4367173673 creator A5017620809 @default.
- W4367173673 creator A5039741966 @default.
- W4367173673 creator A5057695381 @default.
- W4367173673 date "2023-04-27" @default.
- W4367173673 modified "2023-09-30" @default.
- W4367173673 title "Enantio- and Diastereoselective Mannich Reactions of ß-Dicarbonyls by Second Stage Diastereoconvergent Crystallization" @default.
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- W4367173673 doi "https://doi.org/10.1021/acscatal.3c01515" @default.
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