Stereospecific Ring-Expanding Skeletal Rearrangement of Isoindoline to Tetrahydroisoquinoline via a Sequential Aziridine Ring Formation/Opening

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

Heterocycles（2019）

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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-trisubstituted tetrahydroisoquinolines.

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关键词

tetrahydroisoquinoline,sequential aziridine ring-expanding formation/opening,skeletal rearrangement,isoindoline

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