Chiral DBFOX/Ph Complex catalyzed enantioselective nitrone cycloadditions to α,β-unsaturated aldehydes

Organic Letters

Volumn 6, Issue 5, 2004, Pages 675-678

  Shirahase, Moto ^a   Kanemasa, Shuji ^c   Oderaotoshi, Yoji ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN DERIVATIVE; ALDEHYDE DERIVATIVE; MAGNESIUM DERIVATIVE; NICKEL COMPLEX; NITRONE; ZINC COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; COMPLEX FORMATION; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 1642404440     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0361148     Document Type: Article

References (27)

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2. For recent reviews, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449-1458. (c) Gothelf, K. V.; Jørgensen, K. A. Asymmetric Reactions. In Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W., Eds.; John Wiley & Sons: New York, 2002; Chapter 12, pp 817-899.
3. For recent reviews, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449-1458. (c) Gothelf, K. V.; Jørgensen, K. A. Asymmetric Reactions. In Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W., Eds.; John Wiley & Sons: New York, 2002; Chapter 12, pp 817-899.
4. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
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6. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
7. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
8. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
9. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
10. Reactions with two-point binding dipolarophiles: (a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (c) Hori, K. ; Kodama, H.; Ohta, T.; Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950. (d) Jensen, K.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 720, 5840-5841. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004. (h) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6-12. (i) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
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21. General experimental procedures have been described in the Supporting Information for the reactions between nitrone 1a and methacrolein (2) as well as between 1a and α-bromoacrolein (5).
22. In the reactions of 1a to 2 and 5, chemical yields and regio-and diastereoselectivities are given for isoxazolidinecarbaldehydes 3 and 6, while enantioselectivities are given for isoxazolidinemethanols 4 and 7.
23. Enantioselectivities have been determined on the basis of the chiral hplc analysis (Daicel Chiral Cell OD-H) for isoxazolidine methanols 4 and 7.
24. 2 in dichloromethane for a few hours at room temperature. The resulting heterogeneous mixture was used for the subsequent reactions with nitrone s.
25. 2 (Liao, M.-S.; Zhang, Q.; Schwarz, W. H. E. Inorg. Chem. 1995, 34, 5597-5605 ).
26. 2 complexes will be reported elsewhere in near future. Shirahase, M. ; Kanemasa, S.; Hasegawa, M. Manuscript in preparation.
27. X-ray analysis data for 18 and 19 are given in the Supporting Information.