1000004-72-7Relevant academic research and scientific papers
Diastereoselective synthesis of tetrahydrofurans via mead reductive cyclization of keto-β-lactones derived from the tandem Mukaiyama aldol lactonization (TMAL) process
Andrew Mitchell,Romo, Daniel
, p. 9053 - 9059 (2007)
(Chemical Equation Presented) The development of a diastereoselective, three-step strategy for the construction of substituted tetrahydrofurans from alkenyl aldehydes based on the tandem Mukaiyama aldol-lactonization process and Mead reductive cyclization of keto β-lactones is reported. Stereochemical outcomes of the TMAL process are consistent with models established for Lewis acid-mediated additions to α-benzyloxy and β-silyloxy aldehydes while reductions of the five-membered oxocarbenium ions are consistent with Woerpel's models. Further rationalization for observed high diastereoselectivity in reductions of α-silyloxy 5-membered oxocarbenium ions based on stereoelectronic effects are posited. A diagnostic trend for coupling constants of γ-benzyloxy β-lactones was observed that should enable assignment of the relative configuration of these systems.
