A novel phosphine-catalyzed 3+3 annulation of electron-deficient enyne-type propargylic carbonates with α-cyano ketones has been developed, giving tetrasubstituted γ-pyran derivatives in high yields. In this reaction, 1,2,3-butatriene phosphonium intermediates formed in situ acted as dielectrophilic reagents. This represents the first example of electron-deficient enyne-type propargylic carbonates being used as phosphine acceptors in phosphine catalysis.
Jin et al. (Fri,) studied this question.