Asymmetric Synthesis of Cyclobutanone via Lewis Acid Catalyzed Tandem Cyclopropanation/Semipinacol Rearrangement
| Autor: | Su Yong Shim, Do Hyun Ryu, Yuna Choi |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Cyclopropanation Stereochemistry Enantioselective synthesis General Chemistry Chiral Lewis acid 010402 general chemistry Cyclopentanone 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Semipinacol rearrangement chemistry.chemical_compound Colloid and Surface Chemistry chemistry Yield (chemistry) Lewis acids and bases |
| Zdroj: | Journal of the American Chemical Society. 140:11184-11188 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.8b06835 |
| Popis: | Chiral Lewis acid catalyzed asymmetric formation of cyclobutanones from α-silyloxyacroleins and α-alkyl or α-aryl diazoesters has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, various α-silyloxycyclobutanones possessing a chiral β-quaternary center were synthesized in high yield (up to 91%) with excellent enantio- and diastereoselectivity (up to 98% ee and up to >20:1 dr) through tandem cyclopropanation/semipinacol rearrangement. The synthetic potential of this method was illustrated by conversion of the product to various cyclic compounds such as γ-lactone, cyclobutanol, and cyclopentanone. |
| Databáze: | OpenAIRE |
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