Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin
| Autor: | Masahiro Terada, Shigenobu Umemiya |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Formal synthesis chemistry.chemical_compound Transition metal Yield (chemistry) Propargyl Organic chemistry Physical and Theoretical Chemistry Fostriecin Phosphoric acid |
| Zdroj: | Organic Letters. 23:3767-3771 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c01166 |
| Popis: | An enantioselective allylation of silyl-substituted acetylenic aldehydes by chiral phosphoric acid (CPA)/transition metal cooperative catalysis was developed. Enantioenriched homoallylic propargyl alcohols were obtained in good yields with excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the shortest formal synthesis of fostriecin was achieved by the present enantioselective allylation protocol as the key step. The known intermediate of fostriecin reported by McDonald and co-worker was synthesized in only nine steps in 39% total yield. |
| Databáze: | OpenAIRE |
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