Metalated isocyanides: formation, structure, and reactivity

B Altundas, JPR Marrazzo, FF Fleming - Organic & biomolecular …, 2020 - pubs.rsc.org
Metalated isocyanides are highly versatile organometallics. Central to the reactivity of
metalated isocyanides is the presence of two orthogonally reactive carbons, a highly …

An Enantiospecific Synthesis of Isoneoamphilectane Confirms Its Strained Tricyclic Structure

NC Dwulet, Z Chahine, KG Le Roch… - Journal of the …, 2023 - ACS Publications
We describe a total synthesis of the rare isocyanoterpene natural product
isoneoamphilectane and two of its unnatural diastereomers. The significantly strained ring …

Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl–Lithium Exchange–Trapping

LG Mueller Jr, A Chao, E Alwedi, M Natrajan… - Organic …, 2021 - ACS Publications
Oxazoles are rapidly assembled through a sequential deprotonation–condensation of
Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl–lithium exchange …

Dearomatization of aromatic asmic isocyanides to complex cyclohexadienes

B Altundas, E Alwedi, Z Song, AR Gogoi… - Nature …, 2022 - nature.com
A dearomatization-dislocation-coupling cascade rapidly transforms aromatic isocyanides
into highly functionalized cyclohexadienes. The facile cascade installs an exceptional …

Asmic Isocyanide [3+ 2] Cascade to Dihydrooxazoles and Dihydroimidazoles

CVS Kumar, CW Holyoke Jr, TM Keller… - The Journal of Organic …, 2020 - ACS Publications
The versatile isocyanide building block Asmic, anisylsulfanylmethylisocyanide, reacts with
aldehydes and ketones in a BF3· OEt2-mediated condensation to afford thioimidoyl …

Asmic Isocyanide‐Nitrile Isomerization‐Alkylations

E Alwedi, JA Lujan‐Montelongo… - European Journal of …, 2019 - Wiley Online Library
Anisylsulfanylmethylisocyanide, Asmic, is a versatile building block whose alkylations
provide a range of substituted isocyanides. The anisylsulfanyl group plays a critical role in …

Isocyanide purification: C-2 silica cleans up a dirty little secret

A Chao, E Alwedi, FF Fleming - Synthesis, 2019 - thieme-connect.com
EtSiCl 3-treated silica gel,'C-2 silica,'proved exceptionally effective for purifying isocyanides
that are otherwise irreversibly adsorbed during silica gel chromatography. Purification of a …

Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades

JPR Marrazzo, T Huynh, FF Fleming - Synthesis, 2024 - thieme-connect.com
A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient
addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a …

[PDF][PDF] Synthesis of the Isocyanide Building Block Asmic, anisylsulfanylmethylisocyanide

E Alwedi - Organic Syntheses, 2021 - par.nsf.gov
A 3-neck, 500 mL round bottom flask (note 2), equipped with a magnetic stir bar (PTFE-
coated, cylindrical, 3 cm, Figure 1a) was charged with paraformaldehyde (17.7 g, 589 mmol …

Acetonitrile–hexane extraction route to pure sulfonium salts

B Altundas, CVS Kumar, FF Fleming - ACS omega, 2020 - ACS Publications
A rapid, simple procedure is described for synthesizing trialkyl, dialkylaryl, and alkyldiaryl
sulfonium salts that features a selective extraction procedure to access analytically pure …