Journal of Organic Chemistry p. 2029 - 2033 (1992)
Update date:2022-08-03
Topics:
Paleo, M. Rita
Lamas, Carlos
Castedo, Luis
Dominguez, Domingo
The addition of t-BuLi to a low-temperature THF solution of o-bromocarbamates 2 leads to ortho-lithiated intermediates 3, in which internal trapping by the electrophile on the side chain then takes place.This novel Parham-type anionic cyclization procedure affords the variously substituted phthalides 5 in high yields and can also be used for the preparation of lactones 8, which are useful for the synthesis of aristocularine alkaloids.
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