Substrate-controlled, PBu₃-catalyzed annulation of phenacylmalononitriles with allenoates enables tunable access to cyclopentenes

Abstract

Divergence in the PBu3-catalyzed [3+2] annulation of phenacylmalononitriles with allenoates, controlled by the γ-substitution on allenoates, offers a tunable synthesis of multifunctionalized cyclopentene carboxamides and cyclopentenols. An unprecedented formation of...

Chemoselective and one-pot synthesis of novel coumarin-based cyclopenta[c]pyrans via base-mediated reaction of α,β-unsaturated coumarins and β-ketodinitriles

“…The mechanism of the rst step including b-ketodinitriles formation is known. [32][33][34][35][36][37][38]…”

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

“…For explaining the formation of the two kinds of the compounds, a plausible reaction mechanism was proposed on the basis of the previous works [30][31][32][33][34][35] and the present experimental results (Scheme 2). As described in the previous work, TBAF can act as an effective base to catalyze the C-C bond formation via a Michael addition of active methylene groups [31].…”

Piperidine‐Mediated [3+2] Cyclization of Donor‐Acceptor Cyclopropanes and β‐Nitrostyrenes: Access to Polysubsituted Cyclopentenes with High Diastereoselectivity

“…described the phosphine‐catalyzed reaction of phenacylmalononitriles and allenoates for efficient synthesis of substituted methylenecyclopentenecarboxamide (Scheme 1). [5a] …”