N‐Allenyl Amides and O‐Allenyl Ethers in Enantioselective Catalysis

Abstract

Nowadays asymmetric catalysis is an established reality in the organic synthesis community. Nevertheless, the range of applicability both in organic and in organometallic transformations is so large that seeking for new developments seems unstoppable. In this direction, from time to time a new class of "silent" organic compounds rises to prominence and creates new perspectives in the field. Allenyl amides and allenyl A personal dedication: "Asymmetric catalysis represents my personal and primary scientific contact with Prof. Achille Umani-Ronchi. He, together with his ambitious team at the Department of Chemistry 'G. Ciamician' , has contributed substantially in expanding the frontiers of this emerging field since the late 1980s/early 1990s and I took immense advantage of this stimulating environment during my early career in Bologna. The continuing stimulus and encouragement in pursuing unpredictable and non-trivial ultimate goals constitute his 'trademark' as well as personal legacy [

PPh3AuTFA Catalyzed in the Dearomatization of 2-Naphthols with Allenamides

“…In continuation with our ongoing interests in the metal as well as organocatalyzed dearomatization of electron-activated arene, we have recently documented the impact of the gold counterion on the overall chemochemical, regiochemical, and stereochemical outcome of the dearomatization of C2,3-disubstituted indoles with allenamides. , …”

Pd/PC‐Phos‐Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N‐Allenamides

“…Tf ( were determined by single-crystal X-ray diffraction analysis. [22] We next turned to examine whether N-allenamides [23] (4) were applicable to the present reaction. We found that only trace amounts of the corresponding cyclization product 5a were detected under the above reaction conditions (see Scheme 3).…”

Synthesis and Reactivity of N-Allenyl Cyanamides

“…Allenamides, also referred to as N -allenyl amides, are versatile synthetic building blocks in organic chemistry . In comparison to allenamines, which require careful preparation and handling due to their susceptibility toward hydrolysis and polymerization, allenamides exhibit enhanced stability due to delocalization of the nitrogen lone pair of electrons into the electron-withdrawing carbonyl.…”