Asymmetric Synthesis of Fluorinated Monoterpenic Alkaloid Derivatives from Chiral Fluoroalkyl Aldimines via the Pauson-Khand Reaction

摘要

Enantioenriched fluorinated monoterpenic alkaloid analogues were synthesised, employing a strategy based on the previously undescribed diastereoselective propargylation of fluorinated tert-butanesulfinyl imines, and subsequent Pauson-Khand reaction of resulting enyne derivatives, carried out both stoichiometrically and catalytically. The Pauson-Khand reaction tolerated both substituted alkenes and alkynes, and took place in good yields and diastereoselectivities, even when applied to a gram-scale synthesis.