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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.