1444403-40-0Relevant academic research and scientific papers
Chemodivergent Preparation of Various Heterocycles via Phase-Transfer Catalysis: Enantioselective Synthesis of Functionalized Piperidines
Bernardi, Luca,Bertuzzi, Giulio,Fochi, Mariafrancesca,Mazzanti, Andrea,Moimare, Pierluigi,Pecorari, Daniel,Silvestrini, Filippo
, (2020)
In this work, a new chemodivergent domino approach for the preparation of various saturated heterocycles, based on phase-transfer catalysis (PTC), is presented. The versatile nature of doubly electrophilic substrates, showing both a Michael acceptor and a ketone, tethered by a heteroatom, enables three different domino reaction pathways. The nucleophile dictates the chemoselectivity of the reaction. Sulfa-Michael/aldol, cyanide addition/oxa-Michael and Michael/H-shift/aldol processes, along with the variation of the tethering heteroatom, results in the formation of six different classes of saturated heterocycles. DFT calculations account for the observed chemo- and diastereoselectivity of the two most productive processes. Moreover, an extensive investigation on the sulfa-Michael/aldol pathway was carried out, ultimately leading to the development of a new enantioselective domino approach to multi-substituted piperidines based on PTC. (Figure presented.).
Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron transfer
Tarantino, Kyle T.,Liu, Peng,Knowles, Robert R.
, p. 10022 - 10025 (2013/07/26)
Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. Herein, we report the development of a new catalytic protocol fo
