Allylic Lithium Oxyanionic Directed and Facilitated Simmons-Smith Cyclopropanation: Stereoselective Synthesis of (±)-cis-Sabinene Hydrate and a Novel Ring Expansion

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2121-2123

  Cheng, Dai ^a   Kreethadumrongdat, Thanapong ^a   Cohen, Theodore ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

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ARTICLE;

EID: 0006934066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016086y     Document Type: Article

References (37)

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2. (a) Reviews: Simmons, H. E.; Cairns T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. (N. Y.) 1973, 20, 1-131. Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83-134. Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219-41. Subramunian, L. R.; Zeller, K.-P. In Methods of Organic Chemistry (Houben-Weyl); Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1997; Vol. E17a, pp 256-308. Charette, A. B. In Organozine Reagents. A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 263-283.
3. (a) Reviews: Simmons, H. E.; Cairns T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. (N. Y.) 1973, 20, 1-131. Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83-134. Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219-41. Subramunian, L. R.; Zeller, K.-P. In Methods of Organic Chemistry (Houben-Weyl); Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1997; Vol. E17a, pp 256-308. Charette, A. B. In Organozine Reagents. A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 263-283.
4. (a) Reviews: Simmons, H. E.; Cairns T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. (N. Y.) 1973, 20, 1-131. Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83-134. Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219-41. Subramunian, L. R.; Zeller, K.-P. In Methods of Organic Chemistry (Houben-Weyl); Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1997; Vol. E17a, pp 256-308. Charette, A. B. In Organozine Reagents. A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 263-283.
5. (a) Reviews: Simmons, H. E.; Cairns T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. (N. Y.) 1973, 20, 1-131. Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83-134. Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219-41. Subramunian, L. R.; Zeller, K.-P. In Methods of Organic Chemistry (Houben-Weyl); Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1997; Vol. E17a, pp 256-308. Charette, A. B. In Organozine Reagents. A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 263-283.
6. (b) For a discussion of various methods of producing zinc carbenoids and their structures, see: Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 2592-2602.
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10. (a) Winstein, S.; Sonnenberg, J.; DeVries, L. J. Am. Chem. Soc. 1959, 81, 6523-6524. Poulter, C. D.; Friedrich, E. C.; Winstein, S. J. Am. Chem. Soc. 1969, 91, 6892-6894 and references therein.
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12. For an excellent review including directed Simmons-Smith cyclopropanations, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
13. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197-1207. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943-11952 and citations therein. Denmark, S. E.; Christenson, B. L.; O'Conner, S. P.; Murase, N. Pure Appl. Chem. 1996, 68, 23-27.
14. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197-1207. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943-11952 and citations therein. Denmark, S. E.; Christenson, B. L.; O'Conner, S. P.; Murase, N. Pure Appl. Chem. 1996, 68, 23-27.
15. Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197-1207. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943-11952 and citations therein. Denmark, S. E.; Christenson, B. L.; O'Conner, S. P.; Murase, N. Pure Appl. Chem. 1996, 68, 23-27.
16. Some examples: Kelly, D. P.; Leslie, D. R.; Smith, B. D. J. Am. Chem. Soc. 1984, 106, 687-694. Nash, G.; Waring, A. J. J. Chem. Res., Miniprint 1988, 1811-1823. Bessmertnykh, A. G.; Bubnov, Y. N.; Voevodskaya, T. I.; Donskaya, N. A.; Zykov, A. Y. Zh. Org. Khim, 1991, 26, 2348-2355. Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640.
17. Some examples: Kelly, D. P.; Leslie, D. R.; Smith, B. D. J. Am. Chem. Soc. 1984, 106, 687-694. Nash, G.; Waring, A. J. J. Chem. Res., Miniprint 1988, 1811-1823. Bessmertnykh, A. G.; Bubnov, Y. N.; Voevodskaya, T. I.; Donskaya, N. A.; Zykov, A. Y. Zh. Org. Khim, 1991, 26, 2348-2355. Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640.
18. Some examples: Kelly, D. P.; Leslie, D. R.; Smith, B. D. J. Am. Chem. Soc. 1984, 106, 687-694. Nash, G.; Waring, A. J. J. Chem. Res., Miniprint 1988, 1811-1823. Bessmertnykh, A. G.; Bubnov, Y. N.; Voevodskaya, T. I.; Donskaya, N. A.; Zykov, A. Y. Zh. Org. Khim, 1991, 26, 2348-2355. Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640.
19. Some examples: Kelly, D. P.; Leslie, D. R.; Smith, B. D. J. Am. Chem. Soc. 1984, 106, 687-694. Nash, G.; Waring, A. J. J. Chem. Res., Miniprint 1988, 1811-1823. Bessmertnykh, A. G.; Bubnov, Y. N.; Voevodskaya, T. I.; Donskaya, N. A.; Zykov, A. Y. Zh. Org. Khim, 1991, 26, 2348-2355. Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640.
20. Fanta, W. I.; Erman, W. F. J. Org. Chem. 1968, 33, 1656-1659.
21. Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-413.
22. 3). The solvent was removed to give an oily residue that was subjected to column chromatography to give 99 mg (0.64 mmol, 64% yield) of the cyclopropanation product 4.
23. For previous syntheses of (±)-cis-sabinene hydrate 4, see refs 7 and 8 and Gaoni, Y. Tetrahedron 1972, 28, 5525-5531.
24. Woods, G. F.; Griswold, P. H., Jr.; Armbrecht, B. H.; Blumenthal, D. I.; Plapinger, R. J. Am. Chem. Soc. 1950, 72, 1645-1648.
25. 1H NMR spectrum was obtained, but it was not further characterized because of its instability. The 45% yield of 8 was obtained by treating the crude 7 with a catalytic amount of HCl.
26. Wenkert, E.; Buckwalter, B. L.; Sathe, S. S. Synth. Commun. 1973, 3, 261-264.
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32. Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525- 3532. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974-6981.
33. 1H NMR spectrum of the same mixture.
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35. Cheng, D.; Zhu, S.; Yu, Z.; Cohen, T. J. Am. Chem. Soc., 2001, 123, 30-34.
36. The lithium salt of a cyclopent-2-ene-1-ol was reported by Corey and Virgil to be cyclopropanated under Simmons-Smith conditions, and their procedure was then used by Saxton et al. in a very similar system. However there was no indication as to why the lithium salt was used. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. Guile, S. D.; Saxton, J. E.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1992, 1763- 1767.
37. The lithium salt of a cyclopent-2-ene-1-ol was reported by Corey and Virgil to be cyclopropanated under Simmons-Smith conditions, and their procedure was then used by Saxton et al. in a very similar system. However there was no indication as to why the lithium salt was used. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431. Guile, S. D.; Saxton, J. E.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1992, 1763-1767.