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Aerobic Palladium(II)‐Catalyzed 5‐ endo ‐ trig Cyclization: An Entry into the Diastereoselective C‐2 Alkenylation of Indoles with Tri‐ and Tetrasubstituted Double Bonds
Author(s) -
Kandukuri Sandeep R.,
Schiffner Julia A.,
Oestreich Martin
Publication year - 2012
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.201106927
Subject(s) - amide , chemistry , ring (chemistry) , indole test , nitrogen atom , stereochemistry , palladium , double bond , catalysis , cleavage (geology) , combinatorial chemistry , polymer chemistry , organic chemistry , biology , fracture (geology) , paleontology
The endo trick : An endo ring closure onto the trigonal β carbon atom of α,β‐unsaturated acceptors that are tethered to the indole nitrogen atom followed by amide cleavage enables the diastereoselective C‐2 alkenylation of indoles with fully substituted double bonds. The carboxy group functions as a synthetically useful temporary tether (see scheme).