Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis-Hillman reaction.
نویسندگان
چکیده
En route to a photoswitchable interlocked catalyst we have proved the ability of thiodiglycolamide to act as a template in the formation of hydrogen-bonded [2]rotaxanes. X-ray diffraction studies reveal the shielding of the sulfide atom by the macrocycle. A series of molecular shuttles are described as having an isomerizable fumaramide and thiodiglycolamide binding sites for controlling the relative ring position at will. By employing these systems as photoregulated catalysts, the TiCl4-mediated chalcogeno-Morita-Baylis-Hillman reaction is tested. In the presence of the maleamide shuttle, in which the sulfide function is encapsulated by the macrocycle, a complete loss in control of the geometry of the produced aldol is observed. The E-aldol adduct is predominantly obtained when the photoisomerized fumaramide shuttle, in which the sulfide function is exposed, is used.
منابع مشابه
Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis–Hillman reaction† †Electronic supplementary information (ESI) available: Experimental procedures, spectroscopic and mass spectrometry data for all of the new compounds, and the full crystallographic details of 3a. CCDC 1532346. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00724h Click here for additional data file. Click here for additional data file.
متن کامل
Et3N/H2O: A green and inexpensive organocatalytic medium for efficient Baylis-Hillman reaction
A new organocatalyzed method is developed for Baylis–Hillman reactions of cyclohex-2-enone with various aromatic aldehydes in the presence of water and catalytic quantities of triethylamine. All reactions take place at room temperature and relatively good yields of various products are obtained within a time frame which does not exceed 24 hours. The mild reaction conditions used in the present ...
متن کاملEt3N/H2O: A green and inexpensive organocatalytic medium for efficient Baylis-Hillman reaction
A new organocatalyzed method is developed for Baylis–Hillman reactions of cyclohex-2-enone with various aromatic aldehydes in the presence of water and catalytic quantities of triethylamine. All reactions take place at room temperature and relatively good yields of various products are obtained within a time frame which does not exceed 24 hours. The mild reaction conditions used in the present ...
متن کاملThe Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry.
The Baylis-Hillman reaction is a successful, useful, and atom-economical carbon-carbon bond forming reaction, which has grown from an obscure level to the level of high synthetic popularity due to its operational simplicity and also due to the enormous applications of the Baylis-Hillman adducts in organic synthesis. In this tutorial review, we briefly describe the way this reaction has grown to...
متن کاملDifferent Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate
In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausib...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical science
دوره 8 5 شماره
صفحات -
تاریخ انتشار 2017