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Highly Enantioselective Construction of Fused Pyrrolidine Systems That Contain a Quaternary Stereocenter: Concise Formal Synthesis of (+)‐Conessine
Author(s) -
Jiang Biao,
Xu Min
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200353583
Subject(s) - stereocenter , pyrrolidine , enantioselective synthesis , moiety , substituent , stereoselectivity , stereochemistry , cycloaddition , chemistry , organic chemistry , catalysis
No protecting groups were required in a concise and atom‐economical synthesis of the optically active tetracyclic pyrrolidine 3 under mild conditions. A highly diastereoselective Pauson–Khand reaction ( 1 → 2 ) was used to construct the compact tetracycle with its quaternary stereocenter. The stereoselectivity of the cycloaddition was affected by the substituent on the propargylic moiety.