Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization | Zendy

Kempegowda Mantelingu | Zendy; Yingfu Lin | Zendy; Daniel Seidel | Zendy

Open Access

Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization

Author(s) -

Kempegowda Mantelingu,

Yingfu Lin,

Daniel Seidel

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502918g

Subject(s) - chemistry , intramolecular force , stereocenter , piperidine , morpholine , surface modification , benzoic acid , redox , azomethine ylide , medicinal chemistry , catalysis , cycloaddition , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , 1,3 dipolar cycloaddition

Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.

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