Enantioselective intramolecular Pictet–Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones

Abstract

An enantioselective intramolecular Pictet-Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones was developed by using a chiral phosphoric acid as catalyst. This method enabled the construction of a series of chiral isoindolinone...

One-Pot Reaction Sequence: N-Acylation/Pictet–Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues

“…Recent syntheses, which include the aza-Friedel–Crafts reaction as the main step, should be mentioned here as well. , Usually, the first two reactions mentioned above, crucial in the formation of the β-carboline fragment, demand elevated temperatures, and various acidic or organometallic catalysts . These methods, though effective, may pose challenges such as the synthesis and application of complex or difficult to access reagents, , multistage protocols, diastereoselectivity issues, , and a complex apparatus design.…”

Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones

“…2 A number of enantioselective reactions have been developed for the construction of chiral isoindolinones based on the direct transformations of the preexisting isoindolinone ring, 3 including enantioselective nucleophilic substitution of 3-hydroxyisoindolinones, 4 nucleophilic addition of 3-substituted isoindolinones, 5 and annulation of 3-methyleneisoindolinones. 6 In addition, Rh-catalyzed asymmetric [4 + 1] annulation of benzamides with enynes, 7 difluoromethylene alkynes, 8 or diazo derivatives, 9 and Pd-catalyzed intramolecular enantioselective aza-Wacker reaction of benzamides with alkenes 10 also constitute efficient avenues to chiral 3,3′-disubstituted isoindolinones. Despite these notable advances, the development of an efficient method for the formation of chiral 3,3′-disubstituted isoindolinones is still highly desirable.…”

Substrate Controlled [3+3] Relay Catalytic Cyclization of α‐(3‐Isoindolinonyl) Propargylic Alcohols with 5‐Aminoisoxazoles

“…In continuation of our earlier efforts on transformations of isoindolinones [6] and aminoisoxazoles, [7] herein we present a [3 + 3] relay catalytic cyclization [8,9] of α- (3-isoindolinonyl) propargylic alcohols with 5-aminoisoxazoles. Under mild conditions, a variety of spiro-isoindolinone-dihydropyridines as well as isoxazolo [4,5-b]pyridines were achieved in moderate to good yields.…”