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Search for "styrene derivatives" in Full Text gives 51 result(s) in Beilstein Journal of Organic Chemistry.

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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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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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Published 28 Dec 2010

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