Ag(I)-Catalyzed Indolization/C3-Functionalization Cascade of 2‑Ethynylanilines via Ring Opening of Donor–Acceptor Cyclopropanes

A AgSbF₆-catalyzed cascade involving the ring opening of donor–acceptor cyclopropanes (DACs) preceded by the cyclization of <i>N</i>-protected 2-ethynylaniline is described. The method discloses a step-economy route to 2,3-disubstituted indole, where a Ag catalyst is found to trigger the cascade by activating both alkyne and DACs. Various functionalities at different ends of both substrates offer rapid access to 2,3-disubstituted indole derivatives in one pot in good to excellent yields. Elaboration of the cascade product to useful intermediates is also depicted

Enantioselective Hydrophosphonylation of <i>in Situ</i> Generated <i>N</i>‑Acyl Ketimines Catalyzed by BINOL-Derived Phosphoric Acid

An efficient route to pharmacologically interesting isoindolinone-based α-amino phosphonates is described via asymmetric hydrophosphonylation of <i>in situ</i> generated ketimines catalyzed by BINOL-derived phosphoric acid. The reaction proceeds smoothly at ambient temperature affording a variety of α-amino phosphonates with a quaternary stereogenic center embedded in isoindolinone motif in high yields with excellent enantiomeric ratios (up to 98.5:1.5 er). Several interesting transformations of the products into valuable synthetic intermediates are also depicted

Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations

A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields

Ni(II)-Catalyzed Highly Stereo- and Regioselective Syntheses of Isoindolinones and Isoquinolinones from <i>in Situ</i> Prepared Aldimines Triggered by Homoallylation/Lactamization Cascade

An efficient route to isoindolinones and isoquinolinones has been achieved via a domino Ni-catalyzed homoallylation/lactamization from <i>in situ</i> prepared imines, derived from <i>o</i>-formyl benzoates and <i>o</i>-formyl arylacetates, with conjugated dienes promoted by diethylzinc. The reaction proceeds smoothly at room temperature for a variety of aldehydes, amines, and dienes. The method involves one C–C and two C–N bond forming events under operationally simple conditions

Unified Approach to Isoindolinones and THIQs via Lewis Acid Catalyzed Domino Mukaiyama–Mannich Lactamization/Alkylations: Application in the Synthesis of (±)-Homolaudanosine

A novel and efficient synthesis of a variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama–Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (<b>2b</b>) has been achieved using this method

A General Catalytic Route to Isoindolinones and Tetrahydroisoquinolines: Application in the Synthesis of (±)-Crispine A

An unprecedented highly efficient Lewis acid catalyzed one-pot cascade has been demonstrated as a general catalytic system for the synthesis of diversely substituted isoindolinones and tetrahydroisoquinolines. The cascade effects one C–C and two C–N bond-forming events in one pot. Several interesting transformations of the products into valuable synthetic intermediates are featured with the successful total synthesis of (±)-crispine A

An Efficient Entry to <i>syn</i>- and <i>anti</i>-Selective Isoindolinones via an Organocatalytic Direct Mannich/Lactamization Sequence

An organocatalytic direct Mannich–lactamization sequence for the syntheses of pharmacologically important enantioenriched isoindolinones is reported. The method utilizes simple α-amino acids to deliver <i>syn-</i> and <i>anti</i>- selective isoindolinones with remarkably high enantioselectivity (up to >99% ee) in good to excellent yields and diastereomeric ratios. The overall sequence involves one C–C and two C–N bond forming events in one pot starting from inexpensive starting material

An Efficient Entry to <i>syn</i>- and <i>anti</i>-Selective Isoindolinones via an Organocatalytic Direct Mannich/Lactamization Sequence

An organocatalytic direct Mannich–lactamization sequence for the syntheses of pharmacologically important enantioenriched isoindolinones is reported. The method utilizes simple α-amino acids to deliver <i>syn-</i> and <i>anti</i>- selective isoindolinones with remarkably high enantioselectivity (up to >99% ee) in good to excellent yields and diastereomeric ratios. The overall sequence involves one C–C and two C–N bond forming events in one pot starting from inexpensive starting material

(<i>R</i>)‑DM-SEGPHOS–Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions

An efficient diastereo- and enantioselective route to access a wide range of highly substituted pyrrolidine and pyrrolizidine derivatives has been described via (1,3)- and double (1,3)-dipolar cycloaddition reactions catalyzed by the (<i>R</i>)-DM-SEGPHOS–Ag­(I) complex. The reactions proceed smoothly at ambient temperature, affording a variety of pyrrolidines and pyrrolizidines in high yields (up to 93%) with up to 99:1 dr and excellent enantioselectivities (up to 98% ee) without any additives. The newly synthesized pyrrolidine and pyrrolizidine derivatives contain four and seven contiguous stereogenic centers, respectively. Moreover, the synthetic utility of enantioenriched products has been demonstrated by transforming them into various synthetically useful advanced intermediates