Asymmetric aza‐Diels–Alder and Cation–olefin Cyclization Sequence: a Concise Way to Fused Chiral Cyclopenta[ b ]piperidines | Zendy

Li QingZhu | Zendy; Ma Lei | Zendy; Dong Lin | Zendy; Chen YingChun | Zendy

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Asymmetric aza‐Diels–Alder and Cation–olefin Cyclization Sequence: a Concise Way to Fused Chiral Cyclopenta[ b ]piperidines

Author(s) -

Li QingZhu,

Ma Lei,

Dong Lin,

Chen YingChun

Publication year - 2012

Publication title -

chemcatchem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.497

H-Index - 106

eISSN - 1867-3899

pISSN - 1867-3880

DOI - 10.1002/cctc.201200020

Subject(s) - iminium , piperidine , olefin fiber , cationic polymerization , chemistry , sequence (biology) , domino , diels–alder reaction , stereochemistry , medicinal chemistry , organic chemistry , ion , catalysis , biochemistry

An asymmetric aza‐Diels–Alder and cation–olefin cyclization sequence has been developed to construct cyclopenta[ b ]piperidine skeletons with moderate yields and excellent stereoselectivities, by employing 5‐enals and N ‐Ts‐1‐aza‐1,3‐butadienes as the starting materials. A designed domino cation–olefin/Friedel–Crafts reaction verified that the cyclization of N ‐Ts iminium ion underwent a stepwise cationic process.

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