Gold-Catalyzed Divergent N/O-Vinylations of trans-2-Butene-1,4-amino Alcohols with Alkynes and the Cascade Rearrangements/Cyclizations to Dihydropyrroles and Dihydrofurans

Although the transition-metal-catalyzed vinylations ofamines andalcohols via the additions to alkynes have been well developed, theselective vinylations of amino alcohols have been merely investigated.Herein, we report the gold-catalyzed divergent additions of trans-2-butene-1,4-amino alcohols' N-H andO-H groups to alkynes. The allyl enamine and allyl vinyl etheradducts then underwent a cascade (Aza-) Claisen rearrangement/cyclizationsequence, furnishing the functionalized dihydropyrrole and dihydrofuranproducts.

Automated summary

The gold-catalyzed divergent additions of trans-2-butene-1,4-amino alcohols' N-H and O-H groups to alkynes, followed by a cascade (Aza-) Claisen rearrangement/cyclization sequence, has been reported. This reaction produces functionalized dihydropyrrole and dihydrofuran products.