Application of the intramolecular aza-Wittig reaction to the synthesis of vinylogous urethanes and amides

Silver‐Catalyzed Hydroamination: Synthesis of N‐Bridgehead Pyrroles, Incorporating a Protection‐Deprotection Strategy for Preparation of Cyclic Secondary Vinylogous Carbamates

“…They have been prepared from lactim ethers, [10] from azido dicarbonyl compounds, [11] from alkenyl-substituted β-enamino esters, [12] and by lithiation of ketimines [13] amongst others. However, the most common method used for preparation of these compounds is the Eschenmoser sulphide contraction (also known as the Eschenmoser coupling reaction).…”

Total Synthesis of (+)‐Clavolonine, (−)‐Deacetylfawcettiine, and (+)‐Acetylfawcettiine

“…[9] Hence, our retrosynthesis focused on the skeleton of (+)-clavolonine (1; Scheme 3). For this strategy we envisioned the late-stage formation of tertiary amine 1 by a Staudinger/AzaWittig [10] sequence of azide 6 and subsequent Mannich cyclization and N-alkylation.…”

A new conjugated addition of trialkyl phosphites and alkylidenephosphoranes to 3‐ω‐azideoacetyl coumarin synthesis of some 1,2,3,4‐triazaphospholes, triazoles, and azido‐coumarin derivatives

“…As depicted in , a 1,3‐dipolar addition of the azide 1 on the PC bond of the ylide 7b , 7c followed by elimination of TPPO from the cyclic intermediate 9 afforded N ‐1‐substituted‐5‐methyl (or 5‐phenyl)‐1,2,3‐triazoles 10a , 10b [19–23] . The formation of the triazoles from treating 1 with 7a , 7b adequately demonstrates the regiochemistry [23] of the reaction that leads to the exclusive formation of 1,5‐ instead of 1,4‐disubstituted triazoles.…”