Phosphine-Catalyzed Asymmetric Allylic Alkylation of Achiral MBH Carbonates with 3,3′-Bisindolines: Enantioselective Construction of Quaternary Stereogenic Centers
| Autor: | Chuan Xiang Alvin Tan, Guang-Jian Mei, Yixin Lu |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter Catalysis chemistry.chemical_compound Tsuji–Trost reaction chemistry Physical and Theoretical Chemistry Bifunctional Phosphine |
| Zdroj: | Organic Letters. 23:1787-1792 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The asymmetric allylic alkylation (AAA) of achiral Morita-Baylis-Hillman (MBH) carbonates with 3,3'-bisindolines under the catalysis of amino-acid-derived bifunctional phosphines was accomplished. With the AAA approach introduced herein, challenging 3,3'-bisindolines bearing an all-carbon quaternary stereocenter (C3a) have been constructed in good yields with good to excellent enantioselectivties. In addition, the synthetic value of this protocol was demonstrated by the facile synthesis of the core skeleton of gliocladin C. |
| Databáze: | OpenAIRE |
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