DOI: 10.1016/s0040-4039(00)00143-x. The asymmetric cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran

The asymmetric cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran

10.1016/s0040-4039(00)00143-x

Crossref journal-article

Elsevier BV

Tetrahedron Letters (78)

Bibliography

Hennessy, A. J., Malone, Y. M., & Guiry, P. J. (2000). The asymmetric cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran. Tetrahedron Letters, 41(13), 2261â2264.

Authors 3

Alan J Hennessy (first)
Yvonne M Malone (additional)
Patrick J Guiry (additional)

References 14 Referenced 24

For recent reviews: (a) Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1; (b) Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Top. Catal. 1997, 4, 311. (10.1023/A:1019121113063)
Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16 and references cited therein. (10.1016/S0022-328X(98)01049-3)
Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. (10.1021/ja00004a056)
Ozawa, F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505. (10.1016/S0040-4039(00)60453-7)
(a) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200; (10.1002/anie.199602001)
(b) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 11, 1338. (10.1055/s-1997-1341)
Hennessy, A. J.; Malone, Y. M.; Guiry, P. J. Tetrahedron Lett. 1999, 40, 9163. (10.1016/S0040-4039(99)01980-2)
Preliminary work was presented at OMCOS 10, 18–22nd July 1999, Versailles, France, Poster Abstract No. 180.
Selected data for 12: found: C, 80.6; H, 10.3. C14H22O requires C, 80.9; H, 10.2. 1H NMR (270 MHz): δ (CDCl3) 1.30 (3H, s, CH3), 1.35 (3H, s, CH3), 1.50–1.67 (m, 4H, H2C(4′), H2C(5′)), 1.83–2.08 (m, 4H, H2C(3′), H2C(6′)), 5.14 (1H, m, HC(2′), 5.56 (1H, dd, J 1.46, 6.04, HC(3)), 5.73 (1H, m, HC(5)) and 5.77 (1H, dd, J 2.44, 5.86, HC(4)); 13C NMR (67.5 MHz): δ (CDCl3) 22.61 (H2C(4′)), 22.64 (H2C(5′)), 23.65 (H2C(3′)), 25.20 (H2C(6′)), 27.91 (CH3), 28.41 (CH3), 87.27 (C(2)), 89.80 (HC(5)), 124.93 (HC(2′)), 127.39 (HC(3)), 136.16 (HC(4)) and 137.90 (C(1′)); νmax (CH2Cl2) 1620 (w) (CC) cm−1; m/z (eims, 70 eV) 178 (M+, 3%), 167 (7), 151 (10), 109 (35), 97 (60) and 57 (100).
Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 482, 267. (10.1016/0022-328X(92)83236-B)
(a) Malone, Y. Ph.D. Thesis, National University of Ireland, 1998;
(b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2337. (10.1016/S0957-4166(98)00251-1)
Racemic 5-cyclohex-1′-en-1′-yl-2,2-dimethyl-2,5-dihydrofuran 12 required for GC analysis was prepared from 6 and 1-iodocyclohexene using literature procedures: Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603. (10.1016/S0040-4039(00)99075-0)
Hennessy, A. J.; Connolly, D.; Guiry, P. J., unpublished results.

Dates

Type	When
Created	23 years, 1 month ago (July 25, 2002, 5:59 p.m.)
Deposited	6 years, 4 months ago (April 14, 2019, 9:26 p.m.)
Indexed	4 days, 14 hours ago (Sept. 2, 2025, 6:35 a.m.)
Issued	25 years, 6 months ago (March 1, 2000)
Published	25 years, 6 months ago (March 1, 2000)
Published Print	25 years, 6 months ago (March 1, 2000)

Funders 0

None

BibTeX

@article{Hennessy_2000, title={The asymmetric cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran}, volume={41}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/s0040-4039(00)00143-x}, DOI={10.1016/s0040-4039(00)00143-x}, number={13}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Hennessy, Alan J and Malone, Yvonne M and Guiry, Patrick J}, year={2000}, month=mar, pages={2261–2264} }

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