ArticleJournal of the American Chemical Society2018
Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 18 citations in OpenAlex.
- Three-Component Synthesis of γ-Amino Esters with α-Quaternary Carbon Centers via NHC/Photoredox Dual Catalysis.Advanced synthesis & catalysis · 2025Article
- Article
- Stereoselective Synthesis of Benzoylated Gulmirecin A and Disciformycin B.Organic letters · 2025Article
- Lithiated Oppolzer Enolates: Solution Structures, Mechanism of Alkylation, and Origin of Stereoselectivity.Journal of the American Chemical Society · 2022Article
- Cooperative Stereoinduction in Asymmetric Photocatalysis.Journal of the American Chemical Society · 2022Article
- CeClAngewandte Chemie (International ed. in English) · 2021Article
- Wittig Rearrangements of Boron-Based Oxazolidinone Enolates.The Journal of organic chemistry · 2019Article
- Pseudophedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism.Journal of the American Chemical Society · 2019Article
- Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations.Journal of the American Chemical Society · 2019Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Building on structural and mechanistic studies of lithiated enolates derived from acylated oxazolidinones (Evans enolates) and chiral lithiated amino alkoxides, we found that amino alkoxides amplify the enantioselectivity of aldol additions. The pairing of enantiomeric series affords matched and mismatched stereoselectivities. The structures of mixed tetramers showing 2:2 and 3:1 (alkoxide-rich) stoichiometries are determined spectroscopically. Rate and computational studies provide a viable mechanistic and stereochemical model based on the direct reaction of the 3:1 mixed tetramers, but they raise unanswered questions for the 2:2 mixed aggregates.
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Registered trials
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