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Volumn 73, Issue 10, 2008, Pages 3674-3679

Cyclic nitriles: Stereodivergent addition-alkylation-cyclization to cis- and trans-abietanes

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; CATALYST ACTIVITY; OPTIMIZATION; SYNTHESIS (CHEMICAL);

EID: 43449098549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8001062     Document Type: Article
Times cited : (11)

References (84)
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    • (c) Barclay, L. R. C. Cyclialkylation of Aromatics. In Friedel-Crafts and Related Reactions; Olah, G., Ed.; Wiley-Interscience: New York, 1971; pp 785-977.
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    • Related polyene cyclizations appear not to exhibit a selectivity dependence on the nucleophilicity of the aromatic ring, perhaps because of an overriding dependence on adopting the Stork-Eschenmoser π-complexed chair conformation. For an acetoxy-bearing phenyl ring exhibiting excellent selectivity for the trans-abietane, see: Ishihara, K, Ishibashi, H, Yamamoto, H. J. Am. Chem. Soc. 2001, 123, 1505
    • Related polyene cyclizations appear not to exhibit a selectivity dependence on the nucleophilicity of the aromatic ring, perhaps because of an overriding dependence on adopting the Stork-Eschenmoser π-complexed chair conformation. For an acetoxy-bearing phenyl ring exhibiting excellent selectivity for the trans-abietane, see: Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2001, 123, 1505.
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    • For an excellent survey of polyene cyclization geometries, see: b
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    • (2005) Chem. Rev , vol.105 , pp. 4730
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    • Virtually identical ratios are obtained in related arylethyl cyclizations onto tertiary alcohols embedded within decalin scaffolds.34
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    • Although ZrCl4 appears not to have been previously employed in Friedel-Crafts cyclizations, the use of chrial zirconium alkoxides promotes highly enantioselective cyclizations. Blay, G, Fernández, I, Pedro, J. R, Vila, C. Org. Lett. 2007, 9, 2601
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    • 1H NMR analysis of the very clean, crude reaction mixtures for 33b and 33c provided no evidence for the presence of a cis-abietane.
    • 1H NMR analysis of the very clean, crude reaction mixtures for 33b and 33c provided no evidence for the presence of a cis-abietane.


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