One-step synthesis of complex nitrogen heterocycles from lmines and alkyl-substituted maleic anhydrides

Yuchen Tang; James C. Fettinger; Jared T. Shaw

doi:10.1021/ol901018k

One-step synthesis of complex nitrogen heterocycles from lmines and alkyl-substituted maleic anhydrides

Yuchen Tang, James C. Fettinger, Jared T. Shaw

Chemistry

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Substituted maleic anhydrides react with imines to form poly cyclic lactam products. Diastereoselectivity can be controlled by altering the reaction conditions in some cases, and regiochemistry is dictated by the structure of the allylic substituents on the anhydride. Cyclic imines, including dihydro-β-carbolines and dihydroisoquinolines, exhibit the highest level of reactivity in these new annulation reactions.

Original language	English (US)
Pages (from-to)	3802-3805
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	17
DOIs	https://doi.org/10.1021/ol901018k
State	Published - Sep 3 2009

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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abstract = "Substituted maleic anhydrides react with imines to form poly cyclic lactam products. Diastereoselectivity can be controlled by altering the reaction conditions in some cases, and regiochemistry is dictated by the structure of the allylic substituents on the anhydride. Cyclic imines, including dihydro-β-carbolines and dihydroisoquinolines, exhibit the highest level of reactivity in these new annulation reactions.",

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