Ynamides in ring forming transformations

XN Wang, HS Yeom, LC Fang, S He… - Accounts of chemical …, 2014 - ACS Publications
The ynamide functional group activates carbon–carbontriple bonds through an attached
nitrogen atom that bears an electron-withdrawing group. As a result, the alkyne has both …

The thriving chemistry of ketenimines

P Lu, Y Wang - Chemical Society Reviews, 2012 - pubs.rsc.org
Ketenimines are an important class of reactive species and useful synthetic intermediates.
During the last two decades several practical and versatile approaches to ketenimines have …

Ketenimines Generated from Ynamides: Versatile Building Blocks for Nitrogen‐Containing Scaffolds

RH Dodd, K Cariou - Chemistry–A European Journal, 2018 - Wiley Online Library
Using ynamides as readily available starting materials, a single step can generate highly
reactive ketenimines, which can then undergo a variety of transformations. The choice of the …

Divergent CH Insertion–Cyclization Cascades of N‐Allyl Ynamides

HV Adcock, E Chatzopoulou… - Angewandte Chemie, 2015 - Wiley Online Library
Gold carbene reactivity patterns were accessed by ynamide insertion into a C (sp3) H
bond. A substantial increase in molecular complexity occurred through the cascade …

Gold (III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo [3.1. 0] hexan-2-imines

L Song, X Tian, M Rudolph, F Rominger… - Chemical …, 2019 - pubs.rsc.org
We herein report the gold (III)-catalyzed selective annulation of anthranils with N-
allylynamides under mild conditions. By trap** the in situ-generated α-imino gold …

N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1, 3-sulfonyl shift in nitrile synthesis

KA DeKorver, WL Johnson, Y Zhang… - The Journal of …, 2011 - ACS Publications
A detailed study of amidine synthesis from N-allyl-N-sulfonyl ynamides is described here.
Mechanistically, this is a fascinating reaction consisting of diverging pathways that could …

Ketenimine formation catalyzed by a high-valent cobalt carbene in bulky alkoxide ligand environment

A Grass, NS Dewey, RL Lord, S Groysman - Organometallics, 2019 - ACS Publications
High-valent cobalt carbene Co (OR) 2 (═ CPh2)(OR= OC t Bu2Ph) undergoes reaction with
various isocyanides CNR′(CNR′= 2, 6-dimethylphenyl isocyanide, 4-methoxyphenyl …

Carbocyclization Cascades of Allyl Ketenimines via Aza-Claisen Rearrangements of N-Phosphoryl-N-allyl-ynamides

KA DeKorver, XN Wang, MC Walton, RP Hsung - Organic Letters, 2012 - ACS Publications
A series of carbocyclization cascades of allyl ketenimines initiated through a thermal aza-
Claisen rearrangement of N-phosphoryl-N-allyl ynamides is described. Interceptions of the …

Synthesis of Cyclopentenimines from N-Allyl Ynamides via a Tandem Aza-Claisen Rearrangement–Carbocyclization Sequence

XN Wang, GN Winston-McPherson… - The Journal of …, 2013 - ACS Publications
We describe here details of our investigations into Pd-catalyzed and thermal aza-Claisen–
carbocyclizations of N-allyl ynamides to prepare a variety of α, β-unsaturated …

Synthesis of N-(acyloxy)-N-alkynylamides via generation of “C 2” from hypervalent alkynyliodane and a weak base

K Kagami, X Liang, N Ishibashi, S Ohrui… - Chemical …, 2023 - pubs.rsc.org
The first synthesis of N-(acyloxy) ynamides was realized through the coupling of N-(acyloxy)
amides and hypervalent alkynyliodane under mild conditions. This reaction probably …