In this contribution, the first direct and efficient functionalization of the preformed 2-phenyltetrahydropyran (2- PhTHP) nucleus by electrophilic interception of the corresponding α-lithiated derivative by employing sBuLi as the base and THF as the solvent at –78 °C was explored. The presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) proved to be critical to governing reaction feasibility both in polar and apolar solvents and for improving the yield of the reaction.
Toward Customized Tetrahydropyran Derivatives through Regioselective α-Lithiation and Functionalization of 2-Phenyltetrahydropyran
TEMPERINI, Andrea;
2016
Abstract
In this contribution, the first direct and efficient functionalization of the preformed 2-phenyltetrahydropyran (2- PhTHP) nucleus by electrophilic interception of the corresponding α-lithiated derivative by employing sBuLi as the base and THF as the solvent at –78 °C was explored. The presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) proved to be critical to governing reaction feasibility both in polar and apolar solvents and for improving the yield of the reaction.File in questo prodotto:
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