Abstract
AbstractThree distinct strategies for catalytic annulations between ynamides and 1‐yn‐3‐ols are described; the resulting carbo‐ and heterocycles were produced efficiently in one‐pot operations using a gold catalyst. The chemoselectivities of these annulations are controlled by variations of the substituents of the ynamides and the 1‐yn‐3‐ols. This reaction sequence involves initial alkoxylations of ynamides, followed by Claisen rearrangement of propargylic enol ethers, and ends with 6‐endo‐trig cyclizations of 1‐allenyl‐5‐amide intermediates. Among these cascade annulations, the cyclizations of 5‐allenyl‐1‐amides to yield 5,6‐dihydro‐2‐pyranones and 6‐alkylenecyclohex‐2‐ene‐1‐carboxamides are unprecedented in the literature.magnified image
Published Version
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