Cyanation and Cyanomethylation of Trimethylammonium Salts via Electrochemical Cleavage of C–N Bonds

We have developed a practical and mild electrochemical protocol for cyanation and cyanomethylation of trimethylammonium salts through a pathway involving C−N bond cleavage without the need for externally stoichiometric reducing...

S-Triggered Schmidt-type Rearrangement of Vinyl Azides to Access N-Aryl-(trifluoromethylsulfinyl)acetamides

A novel S-induced Schmidt-type rearrangement of vinyl azides with CF3SO2Na is reported, which is mediated by triphosgene (BTC) under mild reaction conditions. A wide range of N-arylated 2-(trifluoromethylsulfinyl)acetamieds, for the...

Discovery of gargantulides B and C, new 52-membered macrolactones from Amycolatopsis sp. Complete absolute stereochemistry of the gargantulide family

Gargantulides B and C, two new and highly complex 52-membered glycosylated macrolactones, were isolated from Amycolatopsis sp. strain CA-230715 during an antibacterial screening campaign. The structures of these giant macrolides...

Silver-catalyzed [3+3]-annulation cascade of alkynyl alcohols and α,β-unsaturated ketones for the regioselective assembly of chromanes

An unprecedented Ag(I)-catalyzed [3+3]-annulation of alkynyl alcohols (5-hexyn-1-ols) and α,β-unsaturated ketones is reported to construct simple to complex chromanes. This transformation begins with hydroalkoxylation of alkynol through C-C triple bond...

Visible light photocatalysis in synthesis of pharmaceutically relevant heterocyclic scaffolds

Visible light and photoredox catalysis have emerged as a powerful and long-lasting tool for organic synthesis, demonstrating the importance of a variety of chemical bond formation methods. Natural products, physiologically...

Synthesis of the C50 Diastereomers of the C33-C51 Fragment of Stambomycin D

As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from...

How electron-deficient Cp ligand facilitates Rh-catalyzed annulations with alkynes

The mechanism and origin of CpX ligand effects on Rh-catalyzed annulations with alkynes were investigated by using DFT calculations and the approach of energy decomposition analysis (EDA). The results reveal...

Carbene-Enabled Ether Activation Through the Formation of Oxonium: A Theoretical View

Here, we report a theoretical investigation of the reactivity and chemoselectivity of carbene-enabled ether activation. The mechanism obtained from DFT calculations revealed that the final products were dependent on the...

A Nickel/Organoboron Catalyzed Metallaphotoredox Platform for C(sp2)–P and C(sp2)–S Bond Construction

Herein, an organoboron photocatalyst, aminoquinolate diarylboron (AQDAB), is utilized collaboratively with nickel catalyst in metallaphotoredox catalyzed C(sp2)–P and C(sp2)–S cross-coupling reactions. This strategy effectively couples aryl halides with diarylphosphine oxides...

Asymmetric catalytic nitrooxylation and azidation of β-keto amides/esters with hypervalent iodine reagents

Chiral Lewis acid-catalyzed enantioselective nitrooxylation of cyclic and acyclic β-keto amides/esters with hypervalent iodine(III) reagents is reported. A number of α-nitrooxy-β-keto amides/esters were obtained with good yields and high enantioselectivities...