Premium
Combining NHC–Cu and Brønsted Base Catalysis: Enantioselective Allylic Substitution/Conjugate Additions with Alkynylaluminum Reagents and Stereospecific Isomerization of the Products to Trisubstituted Allenes
Author(s) -
Dabrowski Jennifer A.,
Haeffner Fredrik,
Hoveyda Amir H.
Publication year - 2013
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.201303501
Subject(s) - enantioselective synthesis , isomerization , allylic rearrangement , chemistry , stereospecificity , stereocenter , alkyne , combinatorial chemistry , catalysis , organic chemistry
All‐catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne‐based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine‐catalyzed isomerization to trisubstituted allenes (see picture; NHC=N‐heterocyclic carbene).