메뉴 건너뛰기




Volumn 6, Issue 19, 2004, Pages 3393-3395

Asymmetric synthesis of α-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 3 METHYLPROLINE; ACETAL DERIVATIVE; IMINE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4644225046     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0485971     Document Type: Article
Times cited : (48)

References (33)
  • 6
    • 0037768402 scopus 로고
    • For reviews on α-amino aldehydes and ketones, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. (b) Fisher, L. E.; Muchowski, J. M. Org Prep. Proced. Int. 1990, 22, 399.
    • (1989) Chem. Rev. , vol.89 , pp. 149
    • Jurczak, J.1    Golebiowski, A.2
  • 7
    • 0010338412 scopus 로고
    • For reviews on α-amino aldehydes and ketones, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. (b) Fisher, L. E.; Muchowski, J. M. Org Prep. Proced. Int. 1990, 22, 399.
    • (1990) Org Prep. Proced. Int. , vol.22 , pp. 399
    • Fisher, L.E.1    Muchowski, J.M.2
  • 8
    • 0043206066 scopus 로고    scopus 로고
    • For a review of the application of 1,3-dithianes in natural product synthesis, see: Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
    • (2003) Tetrahedron , vol.59 , pp. 6147
    • Yus, M.1    Najera, C.2    Foubelo, F.3
  • 15
    • 0001084241 scopus 로고    scopus 로고
    • Rayner, C. M., Ed.; JAI Press: Stamford, CT
    • For reviews on the chemistry of sulfmimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 55, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, in press.
    • (2000) Advances in Sulfur Chemistry , vol.2 , pp. 249-282
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 16
    • 0032358630 scopus 로고    scopus 로고
    • For reviews on the chemistry of sulfmimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 55, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, in press.
    • (1998) Chem. Soc. Rev. , vol.27 , pp. 13
    • Davis, F.A.1    Zhou, P.2    Chen, B.-C.3
  • 17
    • 0036851670 scopus 로고    scopus 로고
    • For reviews on the chemistry of sulfmimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 55, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, in press.
    • (2002) Acc. Chem. Res. , vol.55 , pp. 984
    • Ellman, J.A.1    Owens, T.D.2    Tang, T.P.3
  • 18
    • 4644245718 scopus 로고    scopus 로고
    • in press
    • For reviews on the chemistry of sulfmimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 55, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, in press.
    • (2004) Tetrahedron , pp. 60
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 20
    • 0038345080 scopus 로고    scopus 로고
    • Langille, N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2003, 4, 575. These workers reported the used DMP as a selective method for removal of thioketals and thioacetals.
    • (2003) Org. Lett. , vol.4 , pp. 575
    • Langille, N.F.1    Dakin, L.A.2    Panek, J.S.3
  • 24
    • 0035979053 scopus 로고    scopus 로고
    • Reference 9d of this article
    • For leading references, see: (a) Davis, F. A. Lee, S.; Yan, H.; Titus, D. D. Org. Lett. 2001, 3, 1757. (b) Reference 9d of this article.
  • 27
    • 0035974397 scopus 로고    scopus 로고
    • For earlier asymmetric syntheses of this amino acid, see: (a) Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253. (b) Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695. (c) Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038. (d) Shen, J.-W.; Qin, D.-G.; Zhang, H.-W.; Yao, Z.-J. J. Org. Chem. 2003, 68, 7479. (e) Merio, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5253
    • Noguchi, Y.1    Uchiro, H.2    Yamada, T.3    Kobayashi, S.4
  • 28
    • 0037189184 scopus 로고    scopus 로고
    • For earlier asymmetric syntheses of this amino acid, see: (a) Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253. (b) Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695. (c) Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038. (d) Shen, J.-W.; Qin, D.-G.; Zhang, H.-W.; Yao, Z.-J. J. Org. Chem. 2003, 68, 7479. (e) Merio, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4695
    • Makino, K.1    Kondoh, A.2    Hamada, Y.3
  • 29
    • 0037039910 scopus 로고    scopus 로고
    • For earlier asymmetric syntheses of this amino acid, see: (a) Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253. (b) Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695. (c) Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038. (d) Shen, J.-W.; Qin, D.-G.; Zhang, H.-W.; Yao, Z.-J. J. Org. Chem. 2003, 68, 7479. (e) Merio, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
    • (2002) J. Org. Chem. , vol.67 , pp. 1038
    • Qin, D.-G.1    Zha, H.-Y.2    Yao, Z.-J.3
  • 30
    • 0141566423 scopus 로고    scopus 로고
    • For earlier asymmetric syntheses of this amino acid, see: (a) Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253. (b) Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695. (c) Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038. (d) Shen, J.-W.; Qin, D.-G.; Zhang, H.-W.; Yao, Z.-J. J. Org. Chem. 2003, 68, 7479. (e) Merio, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
    • (2003) J. Org. Chem. , vol.68 , pp. 7479
    • Shen, J.-W.1    Qin, D.-G.2    Zhang, H.-W.3    Yao, Z.-J.4
  • 31
    • 4544257545 scopus 로고    scopus 로고
    • For earlier asymmetric syntheses of this amino acid, see: (a) Noguchi, Y.; Uchiro, H.; Yamada, T.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5253. (b) Makino, K.; Kondoh, A.; Hamada, Y. Tetrahedron Lett. 2002, 43, 4695. (c) Qin, D.-G.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2002, 67, 1038. (d) Shen, J.-W.; Qin, D.-G.; Zhang, H.-W.; Yao, Z.-J. J. Org. Chem. 2003, 68, 7479. (e) Merio, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
    • (2004) Eur. J. Org. Chem. , pp. 776
    • Merio, P.1    Revuelta, J.2    Tejero, T.3    Cicchi, S.4    Goti, A.5
  • 33
    • 4644231507 scopus 로고    scopus 로고
    • Properties of (-)-14 were consistent with literature values. See ref 17d of this article
    • Properties of (-)-14 were consistent with literature values. See ref 17d of this article.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.