STEREOSPECIFIC RING-EXPANDING SKELETAL REARRANGEMENT OF ISOINDOLINE TO TETRAHYDROISOQUINOLINE VIA A SEQUENTIAL AZIRIDINE RING FORMATION/OPENING

摘要

A stereospecific skeletal rearrangement of isoindoline to tetrahydroisoquinoline was developed under Appel reaction conditions using a combination of PPh3 and CCl4. This reaction involves a sequential ring formation/opening of a labile aziridine and enables the construction of a quaternary carbon center, offering a highly useful method for accessing 3,3,4-trisubstitutedtetrahydroisoquinolines.