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Chiral N‐Heterocyclic Carbenes in Natural Product Synthesis: Application of Ru‐Catalyzed Asymmetric Ring‐Opening/Cross‐Metathesis and Cu‐Catalyzed Allylic Alkylation to Total Synthesis of Baconipyrone C
Author(s) -
Gillingham Dennis G.,
Hoveyda Amir H.
Publication year - 2007
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.200700501
Subject(s) - tsuji–trost reaction , metathesis , enantioselective synthesis , carbene , allylic rearrangement , salt metathesis reaction , chemistry , ring (chemistry) , ring closing metathesis , catalysis , total synthesis , stereochemistry , alkylation , combinatorial chemistry , organic chemistry , polymerization , polymer
Chiral carbenes as major players : Two recently discovered chiral N‐heterocyclic carbene (NHC) complexes play a crucial role in a concise enantioselective total synthesis of baconipyrone C (see scheme). An (NHC)Cu complex catalyzes a double asymmetric allylic alkylation (AAA), and an (NHC)Ru complex catalyzes an asymmetric ring‐opening/cross‐metathesis (AROM/CM) to establish the absolute configuration of the target. RCM=ring‐closing metathesis.