p -Anisaldehyde-Photosensitized Sulfonylcyanation of Chiral Cyclobutenes: Enantioselective Access to Cyclic and Acyclic Systems Bearing All-Carbon Quaternary Stereocenters
| Autor: | Jonathan Lusseau, Yannick Landais, Dario M. Bassani, Iman Traboulsi, Lisa Rouvière, Stéphane Massip, Vincent Pirenne, Frédéric Robert |
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| Přispěvatelé: | Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Soutien à la Recherche de l'Institut Européen de Chimie Biologique, Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Européen de Chimie et de Biologie-Université Sciences et Technologies - Bordeaux 1-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Cyclobutanes
Cyclobutene 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Cycloaddition 0104 chemical sciences 3. Good health Sulfone Stereocenter chemistry.chemical_compound Enantiopure drug chemistry Thioether Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2020, 22 (2), pp.575-579. ⟨10.1021/acs.orglett.9b04345⟩ |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.9b04345⟩ |
| Popis: | The photosensitized p-anisaldehyde-mediated addition of sulfonylcyanides onto the π-system of cyclobutenes is shown to afford highly functionalized cyclobutanes in high yields and diastereocontrol. The homochiral cyclobutene precursors are accessible on multigram scale in two steps through an asymmetric [2 + 2] cycloaddition/vinyl thioether reduction sequence. The enantiopure cyclobutylnitriles can be elaborated further through SmI2-mediated ring opening or converted into new enantiopure cyclobutenes through base-mediated sulfone elimination. |
| Databáze: | OpenAIRE |
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