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Search for "cyclooctanes" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Gold(I)-catalyzed enantioselective cycloaddition reactions

Fernando López and
José L. Mascareñas

Beilstein J. Org. Chem. 2013, 9, 2250–2264, doi:10.3762/bjoc.9.264

methods that affords optically active cyclooctanes by means of a catalytic enantioselective process. Also recently, Chen and co-workers demonstrated that gold-activated allenamide species can participate in [3 + 2] cycloadditions with azomethine imines or nitrones under catalysis with Ph3PAuCl/AgOTf or

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Graphical Abstract

Figure 1: Gold-promoted 1,2-acyloxy migration on propargylic systems.

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Scheme 1: Gold-catalyzed enantioselective intermolecular cyclopropanation.

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Scheme 2: Gold-catalyzed enantioselective intramolecular cyclopropanation.

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Scheme 3: Gold-catalyzed cyclohepta-annulation cascade.

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Scheme 4: Application to the formal synthesis of frondosin A.

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Scheme 5: Gold(I)-catalyzed enantioselective cyclopropenation of alkynes.

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Scheme 6: Enantioselective cyclopropanation of diazooxindoles.

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Figure 2: Proposed structures for gold-activated allene complexes.

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Scheme 7: Gold-catalyzed enantioselective [2 + 2] cycloadditions of allenenes.

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Scheme 8: Gold-catalyzed allenediene [4 + 3] and [4 + 2] cycloadditions.

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Scheme 9: Gold-catalyzed enantioselective [4 + 2] cycloadditions of allenedienes.

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Scheme 10: Gold-catalyzed enantioselective [4 + 3] cycloadditions of allenedienes.

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Scheme 11: Gold-catalyzed enantioselective [4 + 2] cycloadditions of allenamides.

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Scheme 12: Enantioselective [2 + 2] cycloadditions of allenamides.

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Scheme 13: Mechanistic rational for the gold-catalyzed [2 + 2] cycloadditions.

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Scheme 14: Enantioselective cascade cycloadditions between allenamides and oxoalkenes.

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Scheme 15: Enantioselective [3 + 2] cycloadditions of nitrones and allenamides.

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Scheme 16: Enantioselective formal [4 + 3] cycloadditions leading to 1,2-oxazepane derivatives.

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Scheme 17: Enantioselective gold(I)-catalyzed 1,3-dipolar [3 + 3] cycloaddition between 2-(1-alkynyl)-2-alken-...

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Scheme 18: Enantioselective [4 + 3] cycloaddition leading to 5,7-fused bicyclic furo[3,4-d][1,2]oxazepines.

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Review

Published 30 Oct 2013

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Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations

Jakub Saadi,
Irene Brüdgam and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, 1229–1245, doi:10.3762/bjoc.6.141

-trig cyclizations to cycloheptanol derivatives have been observed. In examples with high steric hindrance the ketyl–aryl coupling can be a competing process. Keywords: cyclooctanes; ketones; ketyls; medium-sized rings; samarium diiodide; single electron transfer; styrene derivatives; radicals

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Graphical Abstract

Scheme 1: SmI₂-induced cyclizations of styryl-substituted γ-ketoesters A to benzannulated cyclooctanol deriva...

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Scheme 2: Three-step synthesis of precursor 4 starting from siloxycyclopropane derivative 1.

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Scheme 3: Attempted cyclizations of diastereomeric cycloheptanone derivatives 5a and 5b.

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Scheme 4: Samarium diiodide-induced cyclization of γ-ketoester 7a to tricyclic compound 8.

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Scheme 5: Samarium diiodide-induced cyclizations of methyl ketone 4 and iso-propyl ketone 11.

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Figure 1: NOESY-correlation for compound 10.

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Figure 2: NOESY-correlation for compound 9.

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Scheme 6: Assumed transition structures and intermediates A, B, or C for the cyclizations of (2-propenyl)phen...

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Scheme 7: Reductive fragmentation of highly hindered ketoester 14.

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Scheme 8: Samarium diiodide-induced cyclization of phenyl-substituted substrate 16 leading to lactones 17a an...

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Figure 3: Molecular structure (Diamond [52]) of compound 17b.

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Scheme 9: Samarium diiodide-induced cyclizations of (E)-(1-propenyl)phenyl-substituted γ-ketoesters 18, 21, a...

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Figure 4: Proposed transition structure for the cyclization of (E)-1-propenyl-substituted substrates (HMPA li...

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Scheme 10: Attempted samarium diiodide-induced cyclizations with (E)-1-propenyl-substituted precursors 26a and ...

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Scheme 11: Attempted samarium diiodide-induced cyclization of (Z)-1-propenyl-substituted precursor 30.

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Scheme 12: Samarium diiodide-induced cyclizations of γ-ketoesters 33 and 36.

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Scheme 13: Samarium diiodide-induced cyclizations of diastereomeric stilbenyl-substituted γ-ketoesters 38a and ...

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Figure 5: Molecular structure (Diamond [52]) of compound 40.

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Scheme 14: Attempted cyclization of β-dialkyl-substituted styrene derivative 41.

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Scheme 15: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of α-styryl-substituted γ-ke...

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Scheme 16: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of β-styryl-substituted γ-ke...

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Full Research Paper

Published 28 Dec 2010

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