123537-30-4

Upstream product

• 123463-27-4 (S)-5-chloro-1-phenylpentan-1-ol 
• 31848-98-3 1-phenyl-5-chloropentan-1-ol 
• 1059695-87-2 3-benzoyl-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 98-88-4 benzoyl chloride 
• 123463-25-2 (S)-1-{[((S)-5-Chloro-1-phenyl-pentyl)-dimethyl-silanyl]-methyl}-2-methoxymethyl-pyrrolidine 
• 123463-20-7 [(S)-2-(methoxymethyl)pyrrolidinomethyl]dimethyl benzylsilane 
• 5356-99-0 benzyl chloromethyl dimethyl silane 

Relevant academic research and scientific papers

Toward Customized Tetrahydropyran Derivatives through Regioselective α-Lithiation and Functionalization of 2-Phenyltetrahydropyran

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. 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.