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Beilstein J. Org. Chem. 2018, 14, 2999–3010, doi:10.3762/bjoc.14.279
Graphical Abstract
Scheme 1: Synthesis of first Ru-dithiolate metathesis catalysts.
Figure 1: Most efficient Ru-dithiolate catalysts for stereoretentive olefin metathesis with Z- and E-alkenes ...
Figure 2: Selected examples of sterically or electronically modified ruthenium dithiolate complexes.
Figure 3: Model for stereoretentive metathesis proposed by Pederson and Grubbs [3].
Figure 4: Decrease in the benzylidene signal over time upon reaction with (E)-2-hexenyl acetate.
Scheme 2: Selected applications, part 1.
Scheme 3: Selected applications, part 2.
Figure 5: Catalyst loading required for different types of metathesis reactions.
Scheme 4: Proposed catalyst decomposition pathway occurring via attack of the electron-rich sulfide into meth...
Scheme 5: In situ methylene capping strategy for stereoretentive metathesis.
Scheme 6: Stereoretentive cross-metathesis with (Z)-butene (Z-25) as in situ methylene capping agent; selecte...
Scheme 7: Cross metathesis with Z- and E-trisubstituted allylic alcohols.
Scheme 8: In situ synthesis of Ru-3 and application thereof in the cross-metathesis of 12 and 50.
Figure 6: Examples of biologically active and fragrance molecules synthesized by stereoretentive metathesis.
Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263
Figure 1: Possible reaction pathways in conjugate additions of nucleophiles on extended Michael acceptors.
Figure 2: Early reports of conjugate addition of copper-based reagents to extended Michael acceptors.
Figure 3: First applications of copper catalyzed 1,6-ACA in total synthesis.
Scheme 1: First example of enantioselective copper-catalyzed ACA on an extended Michael acceptor.
Scheme 2: Meldrum’s acid derivatives as substrates in enantioselective ACA.
Scheme 3: Reactivity of a cyclic dienone in Cu-catalyzed ACA of diethylzinc.
Scheme 4: Efficiency of DiPPAM ligand in 1,6-ACA of dialkylzinc to cyclic dienones.
Scheme 5: Sequential 1,6/1,4-ACA reactions involving linear aryldienones.
Scheme 6: Unsymmetrical hydroxyalkyl NHC ligands in 1,6-ACA of cyclic dienones.
Scheme 7: Performance of atropoisomeric diphosphines in 1,6-ACA of Et2Zn on cyclic dienones.
Scheme 8: Selective 1,6-ACA of Grignard reagents to acyclic dienoates, application in total synthesis.
Scheme 9: Reactivity of polyenic linear thioesters towards sequential 1,6-ACA/reconjugation/1,4-ACA and produ...
Scheme 10: 1,6-Conjugate addition of trialkylaluminium with regards to cyclic dienones.
Scheme 11: Copper-catalyzed conjugate addition of trimethylaluminium onto nitro dienoates.
Scheme 12: Copper-catalyzed selective 1,4-ACA in total synthesis of erogorgiaene.
Scheme 13: 1,4-selective addition of diethylzinc onto a cyclic enynone catalyzed by a chiral NHC-based system.
Scheme 14: Cu-NHC-catalyzed 1,6-ACA of dimethylzinc onto an α,β,γ,δ-unsaturated acyl-N-methylimidazole.
Scheme 15: 1,4-Selectivity in conjugate addition on extended systems with the concomitant use of a chelating c...
Scheme 16: Cu-NHC catalyzed 1,4-ACA as the key step in the total synthesis of ent-riccardiphenol B.
Scheme 17: Cu-NHC-catalyzed 1,4-selective ACA reactions with enynones.
Scheme 18: Linear dienones as substrates in 1,4-asymmetric conjugate addition reactions of Grignard reagents c...
Scheme 19: 1,4-ACA of trimethylaluminium to a cyclic enynone catalyzed by a copper-NHC system.
Scheme 20: Generation of a sterically encumbered chiral cyclohexanone from a polyunsaturated cyclic Michael ac...
Scheme 21: Selective conversion of β,γ-unsaturated α-ketoesters in copper-catalyzed asymmetric conjugate addit...
Scheme 22: Addition of trialkylaluminium compounds to nitroenynes catalyzed by L9/CuTC.
Scheme 23: Addition of trialkylaluminium compounds to nitrodienes catalyzed by L9/CuTC.
Scheme 24: Copper catalyzed 1,8- and 1,10-ACA reactions.
Beilstein J. Org. Chem. 2015, 11, 1541–1546, doi:10.3762/bjoc.11.169
Scheme 1: Synthesis of [NHC(picolinate)RuCl(indenylidene)] complexes 2 and 4a.
Scheme 2: Synthesis of complex 4a and 4b from (SIPr)(pyridine)RuCl2(indenylidene) (5).
Figure 1: Solid-state structure of complex 4a from single crystal X-ray diffraction. Hydrogens have been omit...
Figure 2: Olefin metathesis profiles in response to TFA equivalents.
Figure 3: Comparison of olefin metathesis profiles for catalysts 2, 4a and 4b after activation with 150 equiv...
Figure 4: Influence of various acids for the activation of 4a in the RCM of DEDAM.