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Dimeric TADDOL Phosphoramidites in Asymmetric Catalysis: Domino Deracemization and Cyclopropanation of Sulfonium Ylides
Author(s) -
Klimczyk Sebastian,
Misale Antonio,
Huang Xueliang,
Maulide Nuno
Publication year - 2015
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.201503851
Subject(s) - sulfonium , cyclopropanation , phosphoramidite , catalysis , bimetallic strip , chemistry , combinatorial chemistry , ligand (biochemistry) , domino , organic chemistry , salt (chemistry) , dna , biochemistry , receptor , oligonucleotide
A gold‐catalyzed asymmetric cyclopropanation of unactivated olefins with sulfonium ylides in the presence of a bimetallic catalyst with a novel dimeric TADDOL‐phosphoramidite ligand is reported. This transformation allows a rare gold‐catalyzed dynamic deracemization of chiral racemic substrates, where the same catalyst is responsible for several synergistic tasks in solution. The products are useful building blocks in synthesis and enable expeditious access to natural products.