Stereoselective coupling of optically active 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides by electroreduction

Tetrahedron Letters

Volumn 40, Issue 46, 1999, Pages 8125-8128

  Kise, Naoki ^a   Hirata, Yoshihiko ^a   Hamaguchi, Takaaki ^a   Ueda, Nasuo ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

Acylation; Coupling reaction; Electrochemistry; Lactones; Oxazolidinones; Reduction

Indexed keywords

ACID ANHYDRIDE; LACTONE; OXAZOLIDINONE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; ELECTROCHEMICAL ANALYSIS; OPTICAL ROTATION; REDUCTION; STEREOCHEMISTRY;

EID: 0033550311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01720-7     Document Type: Article

References (18)

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9. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
10. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
11. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.; Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
12. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
13. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
14. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
15. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
16. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
17. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron: Asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
18. For recent reports for the asymmetric synthesis of β,γ-disubstituted-γ-lactones, see: (a) Ito, T.; Okamoto, S.; Sato, F.Tetrahedron Lett. 1990, 31, 6399-6402. (b) Chang, C.; Fang, J.; Liao, L. J. Org. Chem. 1993, 58, 1754-1761. (c) Rojo, J.;Garcia, M.; Carretero, J. C. Tetrahedron 1993, 49, 9787-9800. (d) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (e) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77-78. (f) Takahata, H.; Uchida, Y.;Momose, T. Tetrahedron Lett. 1994, 35, 4123-4124 and J. Org. Chem. 1995, 60, 5628-5633. (g) Doyle, M. P.; Kalinin, A.V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846. (h) Amigoni, S.; Schulz, J.; Martin, L.; Le Floc'h, Y. Tetrahedron:asymmetry 1997, 8, 1515-1518. (i) Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.