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Gold(I)‐Catalyzed Cycloisomerization of 1,6‐Diynes: Synthesis of 2,3‐Disubstituted 3‐Pyrroline Derivatives
Author(s) -
Zhang DiHan,
Yao LiangFeng,
Wei Yin,
Shi Min
Publication year - 2011
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.201006969
Subject(s) - cycloisomerization , catalysis , chemistry , trifluoromethanesulfonate , combinatorial chemistry , deuterium , stereochemistry , organic chemistry , physics , quantum mechanics
A novel synthetic protocol for the preparation of the title compounds has been developed from a gold‐catalyzed cycloisomerization of 1,6‐diynes containing propargylic ester and arene–yne units. The corresponding nitrogen‐containing five‐membered heterocyclic compounds have been obtained in moderate to good yields (see scheme; DCE=1,2‐dichloroethane, Tf=triflate). A plausible reaction mechanism has been proposed on the basis of deuterium labeling experiments.