Stereoselective Diels-Alder Reactions of Hexachlorocyclopentadiene with Chiral Alkenes: New Insights into the "Inside-Alkoxy" Model of Stereoselectivity

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5728-5731

  Haller, Jan ^a   Niwayama, Satomi ^a   Duh, How Yunn ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000520459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970161u     Document Type: Article

References (30)

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2. For representative examples involving chiral dienophiles and dipolarophiles: (b) Jäger, V.; Schohe, R.; Paulus, E. F. Tetrahedron Lett. 1983, 24, 5501-5504. (c) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (d) Kim, H. R.; Kim, K. M.; Kim, J. N.; Ryu, E. K. Synth. Commun. 1994, 24, 1107-1116. (e) Jäger, V.; Schröter, D. Synthesis 1990, 556-560. (f) Armstrong, S. K.; Collington, E. W.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1994, 515-519. (g) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, Á.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578-8585.
3. For representative examples involving chiral dienophiles and dipolarophiles: (b) Jäger, V.; Schohe, R.; Paulus, E. F. Tetrahedron Lett. 1983, 24, 5501-5504. (c) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (d) Kim, H. R.; Kim, K. M.; Kim, J. N.; Ryu, E. K. Synth. Commun. 1994, 24, 1107-1116. (e) Jäger, V.; Schröter, D. Synthesis 1990, 556-560. (f) Armstrong, S. K.; Collington, E. W.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1994, 515-519. (g) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, Á.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578-8585.
4. For representative examples involving chiral dienophiles and dipolarophiles: (b) Jäger, V.; Schohe, R.; Paulus, E. F. Tetrahedron Lett. 1983, 24, 5501-5504. (c) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (d) Kim, H. R.; Kim, K. M.; Kim, J. N.; Ryu, E. K. Synth. Commun. 1994, 24, 1107-1116. (e) Jäger, V.; Schröter, D. Synthesis 1990, 556-560. (f) Armstrong, S. K.; Collington, E. W.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1994, 515-519. (g) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, Á.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578-8585.
5. For representative examples involving chiral dienophiles and dipolarophiles: (b) Jäger, V.; Schohe, R.; Paulus, E. F. Tetrahedron Lett. 1983, 24, 5501-5504. (c) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (d) Kim, H. R.; Kim, K. M.; Kim, J. N.; Ryu, E. K. Synth. Commun. 1994, 24, 1107-1116. (e) Jäger, V.; Schröter, D. Synthesis 1990, 556-560. (f) Armstrong, S. K.; Collington, E. W.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1994, 515-519. (g) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, Á.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578-8585.
6. For representative examples involving chiral dienophiles and dipolarophiles: (b) Jäger, V.; Schohe, R.; Paulus, E. F. Tetrahedron Lett. 1983, 24, 5501-5504. (c) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (d) Kim, H. R.; Kim, K. M.; Kim, J. N.; Ryu, E. K. Synth. Commun. 1994, 24, 1107-1116. (e) Jäger, V.; Schröter, D. Synthesis 1990, 556-560. (f) Armstrong, S. K.; Collington, E. W.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1994, 515-519. (g) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, Á.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578-8585.
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14. "Anti" and "syn" are not in all cases used according to the IUPAC rules. Instead, it refers to the relative configuration of the medium substituent (M) and the atom, O or C, added to the dipolarophile to form the new stereogenic center. When the carbon chain plus L are drawn in the zig-zag representation, M and the new atom define anti or syn.
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27. A typical reaction was conducted as follows: A mixture of 2-methoxy-3-butene (6) (1.30 g, 15.1 mmol) and hexachlorocyclopentadiene (1) (8.48 g, 31.1 mmol) and 25 mL of toluene was sealed in a Pyrex tube and heated at 100 ± 3 °C for 6 days. The 300 MHz NMR spectrum showed the diastereomer ratio of 71:19 (±2%). Removal of the solvent under reduced pressure gave two products, separated by silica gel column chromatography eluting with 3% ethyl acetate in hexane to give two diastereomers, 6A and 6B, 4.28g (79% yield). Both were purified as colorless oils by Kugelrohr distillation at 93 °C/1.2 mmHg.
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