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Paper | Special issue | Vol 99, No. 2, 2019, pp.1239-1250
Published online, 1st February, 2019
DOI: 10.3987/COM-18-S(F)98
Stereospecific Ring-Expanding Skeletal Rearrangement of Isoindoline to Tetrahydroisoquinoline via a Sequential Aziridine Ring Formation/Opening

Kenichi Kobayashi,* Ryusei Endo, Yusuke Honma, Emi Kasahara, Haruka Saito, Kosaku Tanaka III, Momoko Suzuki, and Hiroshi Kogen*

*Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

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-trisubstituted tetrahydroisoquinolines.