Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of 7-Oxabenzonorbornadienes with Methanol

A DFT Study on the Mechanism and Origin of Regioselectivity in the Rhodium/Diene‐Catalyzed Ring‐Opening Reactions of C1‐Substituted Oxabenzonorbornadienes with Arylboronic Acids

“…Of particular interest are nucleophilic ring‐opening reactions of oxabicyclic alkenes, as they provide access to a broad family of synthetic building blocks bearing multiple stereocenters in a single step [6] with many of these functionalized intermediates useful in natural product synthesis and as motifs in medicinal chemistry [7a,b] . Such ring‐opening reactions have been carried out using a variety of carbon and heteroatom nucleophiles in the presence of Pd, [8a–f] Ni, [9a–d] Ru, [10] , Ir, [11a–c] and Rh [12a–e] complexes.…”

Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

“…The transition-metal-catalyzed ring opening reactions of heterobicyclic alkenes have received intense attention in the past decade as they represent versatile approaches for chiral hydronaphthalenes, which are frequently found in a plethora of natural products and biologically active molecules . The group of Lautens has taken the lead in exploring rhodium-catalyzed asymmetric ring opening reactions (ARO) of heterobicyclic alkenes; and some other groups have also achieved a lot of success by using iridium, nickel, palladium, copper, and ruthenium catalysts . Our group has long had an interest in this kind of reaction and has studied it with co-catalytic systems comprising chiral transition-metal complexes and Lewis acids as previously employed by pioneers in the field. , Followed by our previous work that employing alkynes, amines, phenols, alcohols, and organic acids as nucleophiles, the asymmetric ring-opening reaction of heterobicyclic alkenes by boronic acids has attracted our attention as they offered a straightforward method for the preparation of chiral aryltetralins, which are common substructures in bioactive natural products such as chelidonine, corynoline, and wailupemycin D .…”

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

“…Over the years, several interesting transformations have been investigated such as cycloadditions 4 [18][19][20][21][22][23], dimerizations 3 [24][25][26][27], isomerizations [28][29][30][31], among other reactions that have been reported [32][33][34][35][36][37][38]. The nucleophilic ring-opening reactions of heterobicyclic alkenes are of particular interest [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53], as they provide access to a broad family of synthetic building blocks bearing multiple stereocenters in a single step 2 [54]. Application of these functionalized intermediates have found use in the total synthesis of (+)-norchelidonine (an isoquinoline alkaloid) [55], sertraline (an antidepressant) [56], and arnottin I (an antiinflammatory) [57].…”