Toward Customized Tetrahydropyran (cas 142-68-7) Derivatives through Regioselective α‐Lithiation and Functionalization of 2‐PhenylTetrahydropyran (cas 142-68-7)
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Add time:09/29/2019 Source:infona.pl
In this contribution, the first direct and efficient functionalization of the preformed 2‐phenylTetrahydropyran (cas 142-68-7) (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. Both carbon‐ and heteroatom‐based halides were found to be competent electrophiles for this transformation, as well as aliphatic and aromatic aldehydes and ketones, isocyanates, and carboxylic acid derivatives. The combination of hexane/TMEDA lowered the rate of racemization of α‐lithiated optically active 2‐PhTHP, which thereby enabled calculation of its barrier to inversion at –78 °C.
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