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A Pd–H/Isothiourea Cooperative Catalysis Approach to anti-Aldol Motifs: Enantioselective -Alkylation of Esters with Oxyallenes
- Publication Year :
- 2022
- Publisher :
- American Chemical Society (ACS), 2022.
-
Abstract
- The biological and therapeutic significance of polyketides is a powerful impetus for the development of efficient methods to facilitate their construction. Emulating the efficiency of polyketide biosynthesis, a sophisticated arsenal of aldol-based strategies has evolved that is contingent on the generation of single enolate isomers. Since this has the potential to compromise efficiency in reagent-based paradigms, direct catalysis-based solutions would be enabling. To complement the array of substrate-based strategies, and regulate enolate geometry at the catalyst level, a direct catalytic alkylation of esters with oxyallenes has been developed. Synergizing metal hydride reactivity with Lewis base catalysis has resulted in a broad reaction scope with useful levels of stereocontrol (up to >99% ee). Facile derivatization of these ambiphilic linchpins is demonstrated, providing access to high-value vicinal stereocenter-containing motifs, including 1,2-amino alcohols.
Details
- Database :
- OpenAIRE
- Accession number :
- edsair.doi...........7b6434692626ad4e8318899c1da28f42