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 | Zendy

Gillingham Dennis G. | Zendy; Hoveyda Amir H. | Zendy

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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.

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