Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation–Isomerization of Chiral Allenamides and their Applications in Diels–Alder Cycloadditions

Abstract

A series of de novo 3-amido-dienynes was synthesized via tandem α-propargylation–isomerization of chiral allenamides with moderate E/Z ratio. Reactivities of E-and Z-isomers were examined.

Recent progress in transition-metal-free functionalization of allenamides

“…Recently, the same group described a tandem propargylation-1,3-H-shi sequence of chiral allenamides 101 to access both E and Z isomers of chiral 3-amidodienynes (Scheme 27). 34 Moreover, the application of (Z)-3-amidodienynes 102 in Diels-Alder cycloadditions gave endo-II products 103 in good yields and excellent selectivity, while the reactivity of the corresponding (E)-3-amidodienynes toward electrocyclization was inadequate.…”