Enantio- and Diastereoselective Dehydrative 'One-Step' Construction of Spirocarbocycles via a Ru/H+-Catalyzed Tsuji-Trost Approach
| Autor: | Namdev Vatmurge, Yusuke Suzuki, Shinji Tanaka, Masato Kitamura |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Ketone 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Stereocenter Ruthenium Intramolecular force Yield (chemistry) |
| Zdroj: | Chemistry - An Asian Journal. 12:633-637 |
| ISSN: | 1861-4728 |
| DOI: | 10.1002/asia.201700013 |
| Popis: | Chiral spirocarbocyclic skeletons are ubiquitous in natural products. An intramolecular Tsuji-Trost (T-T) α-allylation of simple cyclic ketones is a reasonable approach to construct chiral spriocarbocyclic motifs; however, it has been a challenging approach despite many excellent intermolecular examples. For the first time, this has been achieved by a Ru/H+ combined catalyst that dehydratively cyclizes racemic allylic alcohols comprising a simple ketone via simultaneous activation of the C=O and OH groups. This chiral technology facilitates the construction of various spirocarbocycles containing two contiguous spiro all-carbon quaternary and tertiary stereocenters. Among four possible stereoisomers, one stereoisomer can be selectively produced in high yield, enhancing the feasibility of the T-T strategy, particularly in the synthesis of spirocarbocycles. |
| Databáze: | OpenAIRE |
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