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Specificity of the reaction of (−)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}xethanone with ethenylmagnesium bromide

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Abstract

Ethenylmagnesium bromide (1.5 equiv) forms a chelate with (−)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl} ethanone in THF and promotes its fast primary α-ketol rearrangement into 1-ethenyl-2-hydroxy-2,8,8-trimethylbicyclo[3.2.1]octan-3-one. The latter reacts with excess magnesium reagent (0.5 equiv) according to common 1,2-addition pattern at the carbonyl group and is simultaneously involved in the second α-ketol rearrangement which leads to 1-ethenyl-3-hydroxy-3,8,8-trimethylbicyclo[3.2.1]octan-2-one as thermodynamically more stable regioisomer.

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References

  1. Money, T., Nat. Prod. Rep., 1985, vol. 2, p. 253.

    Article  CAS  Google Scholar 

  2. Fischer, N. and Opitz, G., Organic Synthesis, New York: Wiley, 1973, vol. 5, p. 877.

    Google Scholar 

  3. Vostrikov, N.S., Abutkov, A.V., and Miftakhov, M.S., Izv. Ross. Akad. Nauk, Ser. Khim., 2001, p. 1181.

  4. Grubbs, R.H. and Chang, S., Tetrahedron, 1998, vol. 54, p. 4413.

    Article  CAS  Google Scholar 

  5. Yang, T.-F., Zhang, Z.-N., Tseng, C.-H, and Chen, L.-H., Tetrahedron Lett., 2005, vol. 46, p. 1917.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    N. S. Vostrikov, V. Z. Vasikov & M. S. Miftakhov

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  1. N. S. Vostrikov
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  2. V. Z. Vasikov
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  3. M. S. Miftakhov
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Original Russian Text © N.S. Vostrikov, V.Z. Vasikov, M.S. Miftakhov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 982–985.

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Vostrikov, N.S., Vasikov, V.Z. & Miftakhov, M.S. Specificity of the reaction of (−)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}xethanone with ethenylmagnesium bromide. Russ J Org Chem 42, 962–965 (2006). https://doi.org/10.1134/S1070428006070050

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  • DOI: https://doi.org/10.1134/S1070428006070050

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