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Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118
Graphical Abstract
Scheme 1: Planned Heck reaction of A to compound B and serendipitous discovery of the palladium-catalyzed cyc...
Scheme 2: Synthesis of compounds A (1–6) via methyl 2-siloxycyclopropanecarboxylates D, their alkylation to E...
Scheme 3: Palladium-catalyzed reactions of methyl ketone 1 to tetralin derivative 7 and of isopropyl-substitu...
Scheme 4: Palladium-catalyzed cyclization of diastereomeric cyclopentanone derivatives 3a/3b to products 11a ...
Figure 1: Molecular structure (ORTEP, [14]) of compound 12a (thermal ellipsoids at 50% probability).
Scheme 5: Palladium-catalyzed cyclizations of diastereomeric cyclohexanone derivatives 4a and 4b leading ster...
Figure 2: Molecular structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability).
Scheme 6: Palladium-catalyzed cyclizations of cycloheptanone derivatives 5a and 5b leading to products 15a an...
Figure 3: Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability).
Figure 4: Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability).
Scheme 7: Palladium-catalyzed cyclization of p-methoxy-substituted aryl iodide 6a/6b to compound 16.
Scheme 8: Typical palladium-catalyzed cyclization of an o-iodoaniline derivative to a tricyclic tertiary alco...
Scheme 9: Proposed transition state (TS) explaining the stereoselective formation of cyclization products.
Scheme 10: Possible mechanism of the reduction of palladium(II) to palladium(0) by triethylamine (additional l...
Beilstein J. Org. Chem. 2010, 6, 1229–1245, doi:10.3762/bjoc.6.141
Scheme 1: SmI2-induced cyclizations of styryl-substituted γ-ketoesters A to benzannulated cyclooctanol deriva...
Scheme 2: Three-step synthesis of precursor 4 starting from siloxycyclopropane derivative 1.
Scheme 3: Attempted cyclizations of diastereomeric cycloheptanone derivatives 5a and 5b.
Scheme 4: Samarium diiodide-induced cyclization of γ-ketoester 7a to tricyclic compound 8.
Scheme 5: Samarium diiodide-induced cyclizations of methyl ketone 4 and iso-propyl ketone 11.
Figure 1: NOESY-correlation for compound 10.
Figure 2: NOESY-correlation for compound 9.
Scheme 6: Assumed transition structures and intermediates A, B, or C for the cyclizations of (2-propenyl)phen...
Scheme 7: Reductive fragmentation of highly hindered ketoester 14.
Scheme 8: Samarium diiodide-induced cyclization of phenyl-substituted substrate 16 leading to lactones 17a an...
Figure 3: Molecular structure (Diamond [52]) of compound 17b.
Scheme 9: Samarium diiodide-induced cyclizations of (E)-(1-propenyl)phenyl-substituted γ-ketoesters 18, 21, a...
Figure 4: Proposed transition structure for the cyclization of (E)-1-propenyl-substituted substrates (HMPA li...
Scheme 10: Attempted samarium diiodide-induced cyclizations with (E)-1-propenyl-substituted precursors 26a and ...
Scheme 11: Attempted samarium diiodide-induced cyclization of (Z)-1-propenyl-substituted precursor 30.
Scheme 12: Samarium diiodide-induced cyclizations of γ-ketoesters 33 and 36.
Scheme 13: Samarium diiodide-induced cyclizations of diastereomeric stilbenyl-substituted γ-ketoesters 38a and ...
Figure 5: Molecular structure (Diamond [52]) of compound 40.
Scheme 14: Attempted cyclization of β-dialkyl-substituted styrene derivative 41.
Scheme 15: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of α-styryl-substituted γ-ke...
Scheme 16: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of β-styryl-substituted γ-ke...