Organoselenium compounds: Chemistry and applications in organic synthesis

JM Sonego, SI De Diego, SH Szajnman… - … A European Journal, 2023 - Wiley Online Library
Selenium, originally described as a toxin, turns out to be a crucial trace element for life that
appears as selenocysteine and its dimer, selenocystine. From the point of view of drug …

Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications

CC Lynch, A Sripada, C Wolf - Chemical Society Reviews, 2020 - pubs.rsc.org
Ynamides are among the most powerful building blocks in organic synthesis and have
become invaluable starting materials for the construction of multifunctional compounds and …

Reversal of regioselectivity in ynamide chemistry

B Zhou, TD Tan, XQ Zhu, M Shang, LW Ye - Acs Catalysis, 2019 - ACS Publications
Ynamides are special alkynes bearing an electron-withdrawing group on the nitrogen atom,
and they have been extensively studied over the past decade. However, the addition of …

Direct synthesis of enamides via electrophilic activation of amides

P Spieß, M Berger, D Kaiser… - Journal of the American …, 2021 - ACS Publications
A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction
employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the …

Radical reactions of ynamides

TD Tan, ZS Wang, PC Qian, LW Ye - Small Methods, 2021 - Wiley Online Library
Ynamides are electron‐rich heteroatom‐substituted alkynes with C− C triple bond directly
tethered to the amide group. Over the past decades, ynamides have proven to be versatile …

Highly enantioselective synthesis of propargyl amides through Rh-catalyzed asymmetric hydroalkynylation of enamides: scope, mechanism, and origin of selectivity

XY Bai, WW Zhang, Q Li, BJ Li - Journal of the American Chemical …, 2018 - ACS Publications
Chiral propargyl amides are particularly useful structural units in organic synthesis. The
enantioselective synthesis of propargyl amide is highly desirable. Conventional approach …

Three Component syn‐1,2‐Arylmethylation of Internal Alkynes**

S Dutta, AK Sahoo - Angewandte Chemie International Edition, 2023 - Wiley Online Library
A Pd‐catalyzed three‐component syn‐1, 2‐arylmethylation of internal alkynes
(ynamides/yne‐acetates/alkynes) is described. The readily available and bench stable …

Diorganyl diselenides and iron (III) chloride drive the regio-and stereoselectivity in the selenation of ynamides

TAC Goulart, DF Back, S Moura E. Silva… - The Journal of Organic …, 2020 - ACS Publications
We report here our results on the application of ynamides as substrates in the reactions with
diorganyl dichalcogenides and iron (III) chloride to give selectively three different types of …

Iron-catalyzed acyl migration of tertiary α-azidyl ketones: Synthetic approach toward enamides and isoquinolones

T Yang, X Fan, X Zhao, W Yu - Organic Letters, 2018 - ACS Publications
This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by
treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1, 2 …

Catalytic enantioselective ynamide additions to isatins: Concise access to oxindole alkaloids

M Moskowitz, C Wolf - Angewandte Chemie, 2019 - Wiley Online Library
The highly enantioselective addition of terminal ynamides to a variety of isatins, catalyzed by
a bisoxazolidine copper complex under mild, base‐free reaction conditions, is described …