Triton B-promoted regioselective intramolecular addition of enolates to tethered ynamides for the construction of 8-membered O-heterocycles

Abstract

The synthesis of natural products containing eight-membered heterocycles has proved to be highly challenging. In this contribution, an environmentally benign synthesis of benzo-1,5 dioxocines via ynamides is reported. A new...

Construction of C–N and C–O bonds based on N-allenamide functionalization

“…We also described a synthesis of benzo-1,5-dioxocines 169 from ynamides tethered to propargylic ethers 167 using a key intramolecular hydroalkoxylation of N -allenamides 168 . 49 N -Allenamides substituted with phenyl ethers 168 were generated in situ by treatment of ynamides 167 with Triton B. Regioselective proximal O -alkylation on the N -allenamides led to shelf-stable eight-membered-heterocycles 169 by a sustainable and green approach (Scheme 41).…”

Catalytic intermolecular hydrofunctionalizations of ynamides

“…[1][2][3][4][5] Because of their unique structural characteristics and potential coordination ability, ynamides have now emerged as versatile building blocks in organic synthesis and a variety of intriguing reactivities have been disclosed. [6][7][8][9][10] Some special topics such as intra- [11][12][13][14][15][16] and inter-molecular annulations, [17][18][19][20][21][22] radical reactions, 23,24 and asymmetric transformations 25,26 have been carefully reviewed in the last few years.…”