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Nickel(0)-catalyzed enantioselective annulations of alkynes and arylenoates enabled by a chiral NHC ligand: efficient access to cyclopentenones.
Angew Chem Int Ed Engl. 2014 Nov 24; 53(48):13229-33.AC

Abstract

Cyclopentenones are versatile structural motifs of natural products as well as reactive synthetic intermediates. The nickel-catalyzed reductive [3+2] cycloaddition of α,β-unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C1-symmetric N-heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand provided the cyclopentenone products in very high enantioselectivity and led to a regioselective incorporation of unsymmetrically substituted alkynes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ahlin JS
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.
Donets PA
No affiliation info available
Cramer N
No affiliation info available

MeSH

AlkynesCatalysisCyclopentanesLigandsMolecular StructureNickelStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25258104

Citation

Ahlin, Joachim S E., et al. "Nickel(0)-catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled By a Chiral NHC Ligand: Efficient Access to Cyclopentenones." Angewandte Chemie (International Ed. in English), vol. 53, no. 48, 2014, pp. 13229-33.
Ahlin JS, Donets PA, Cramer N. Nickel(0)-catalyzed enantioselective annulations of alkynes and arylenoates enabled by a chiral NHC ligand: efficient access to cyclopentenones. Angew Chem Int Ed Engl. 2014;53(48):13229-33.
Ahlin, J. S., Donets, P. A., & Cramer, N. (2014). Nickel(0)-catalyzed enantioselective annulations of alkynes and arylenoates enabled by a chiral NHC ligand: efficient access to cyclopentenones. Angewandte Chemie (International Ed. in English), 53(48), 13229-33. https://doi.org/10.1002/anie.201408364
Ahlin JS, Donets PA, Cramer N. Nickel(0)-catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled By a Chiral NHC Ligand: Efficient Access to Cyclopentenones. Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13229-33. PubMed PMID: 25258104.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel(0)-catalyzed enantioselective annulations of alkynes and arylenoates enabled by a chiral NHC ligand: efficient access to cyclopentenones. AU - Ahlin,Joachim S E, AU - Donets,Pavel A, AU - Cramer,Nicolai, Y1 - 2014/09/24/ PY - 2014/08/19/received PY - 2014/9/27/entrez PY - 2014/9/27/pubmed PY - 2015/9/17/medline KW - annulation KW - asymmetric catalysis KW - carbenes KW - cyclopentenones KW - nickel SP - 13229 EP - 33 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 48 N2 - Cyclopentenones are versatile structural motifs of natural products as well as reactive synthetic intermediates. The nickel-catalyzed reductive [3+2] cycloaddition of α,β-unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C1-symmetric N-heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand provided the cyclopentenone products in very high enantioselectivity and led to a regioselective incorporation of unsymmetrically substituted alkynes. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25258104/Nickel_0__catalyzed_enantioselective_annulations_of_alkynes_and_arylenoates_enabled_by_a_chiral_NHC_ligand:_efficient_access_to_cyclopentenones_ DB - PRIME DP - Unbound Medicine ER -