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.
†Department of Chemistry, Indian Institute of Technology Kanpur-208 016, UP, India.
Sivasankaran
S
Dhanasekaran
‡Department of Chemistry, Indian Institute of Science Education and Research Bhopal-462 066, MP, India.
Vishnumaya
V
Bisai
‡Department of Chemistry, Indian Institute of Science Education and Research Bhopal-462 066, MP, India.
Rajshekhar A
RA
Unhale
‡Department of Chemistry, Indian Institute of Science Education and Research Bhopal-462 066, MP, India.
Arun
A
Suneja
†Department of Chemistry, Indian Institute of Technology Kanpur-208 016, UP, India.|‡Department of Chemistry, Indian Institute of Science Education and Research Bhopal-462 066, MP, India.
Vinod K
VK
Singh
D002384:Catalysis; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D054833:Isoindoles; D007546:Isoquinolines; D058116:Lewis Acids; D044005:Tetrahydroisoquinolines; C523713:crispine A