메뉴 건너뛰기




Volumn , Issue 21, 2007, Pages 3503-3507

A practical gold-catalyzed route to 4-substituted oxazolidin-2-ones from N-Boc propargylamines

Author keywords

1,3 Allylic interactions; Gold; Isomerization; Oxazolidinones

Indexed keywords


EID: 34447576888     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700210     Document Type: Article
Times cited : (111)

References (44)
  • 1
    • 33646580706 scopus 로고    scopus 로고
    • Asymmetric protonation: a L.-L. Huang, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2006, 128, 5624-5625;
    • Asymmetric protonation: a) L.-L. Huang, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2006, 128, 5624-5625;
  • 4
    • 33746641275 scopus 로고    scopus 로고
    • Desymmetrization: d F. Zhang, J. M. Fox, Org. Lett. 2006, 8, 2965-2968.
    • Desymmetrization: d) F. Zhang, J. M. Fox, Org. Lett. 2006, 8, 2965-2968.
  • 5
    • 33746146011 scopus 로고    scopus 로고
    • Diels-Alder reaction: e J. Qi, W. R. Roush, Org. Lett. 2006, 8, 2795-2798.
    • Diels-Alder reaction: e) J. Qi, W. R. Roush, Org. Lett. 2006, 8, 2795-2798.
  • 6
    • 0012016624 scopus 로고    scopus 로고
    • Asymmetric aldol: f D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129;
    • Asymmetric aldol: f) D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129;
  • 8
    • 30144439321 scopus 로고    scopus 로고
    • Alkylation: h N. Alouane, F. Bernaud, J. Marrot, E. Vrancken, P. Mangeney, Org. Lett. 2005, 7, 5797-5800 .
    • Alkylation: h) N. Alouane, F. Bernaud, J. Marrot, E. Vrancken, P. Mangeney, Org. Lett. 2005, 7, 5797-5800 .
  • 9
    • 33746191442 scopus 로고    scopus 로고
    • Cycloaddition: i S. D. Bull, S. G. Davies, A. C. Garner, D. Kruchinin, M.-S. Key, P. M. Roberts, E. D. Savory, A. D. Smith, J. E. Thompson, Org. Biomol. Chem. 2006, 4, 2945-2964.
    • Cycloaddition: i) S. D. Bull, S. G. Davies, A. C. Garner, D. Kruchinin, M.-S. Key, P. M. Roberts, E. D. Savory, A. D. Smith, J. E. Thompson, Org. Biomol. Chem. 2006, 4, 2945-2964.
  • 10
    • 2842567030 scopus 로고    scopus 로고
    • Linezolid (Zyvox) as a representative example: a) S. J. Brickner, Curr. Pharm. Des. 1996, 2, 175-194;
    • Linezolid (Zyvox) as a representative example: a) S. J. Brickner, Curr. Pharm. Des. 1996, 2, 175-194;
  • 18
    • 0001684941 scopus 로고    scopus 로고
    • N. S. Barta, D. R. Sidler, K. B. Somerville, S. A. Weissman, R. D. Larsen, P. J. Reider, Org. Lett. 2000, 2, 2821-2824 and references cited therein;
    • c) N. S. Barta, D. R. Sidler, K. B. Somerville, S. A. Weissman, R. D. Larsen, P. J. Reider, Org. Lett. 2000, 2, 2821-2824 and references cited therein;
  • 26
    • 33845546747 scopus 로고    scopus 로고
    • For the latest reviews on gold catalysis, see: g
    • For the latest reviews on gold catalysis, see: g) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7896-7936
    • Hashmi, A.S.K.1    Hutchings, G.J.2
  • 28
    • 34447551218 scopus 로고    scopus 로고
    • th International Symposium on Chirality, June 25-28, 2006 (abstract due date April 30, 2006), Busan, Korea.
    • th International Symposium on Chirality, June 25-28, 2006 (abstract due date April 30, 2006), Busan, Korea.
  • 29
    • 33745450775 scopus 로고    scopus 로고
    • I-catalyzed route to 5-methylene-oxazolidin- 2-ones appeared while this manuscript was in preparation: b R. Robles-Machín, J. Adrio, J. C. Carretero, J. Org. Chem. 2006, 71, 5023-5026;
    • I-catalyzed route to 5-methylene-oxazolidin- 2-ones appeared while this manuscript was in preparation: b) R. Robles-Machín, J. Adrio, J. C. Carretero, J. Org. Chem. 2006, 71, 5023-5026;
  • 34
    • 28244442871 scopus 로고    scopus 로고
    • For a related one-pot protocol, see: b
    • For a related one-pot protocol, see: b) X. Guinchard, Y. Vallée, J.-N. Denis, Org. Lett. 2005, 7, 5147-5150;
    • (2005) Org. Lett , vol.7 , pp. 5147-5150
    • Guinchard, X.1    Vallée, Y.2    Denis, J.-N.3
  • 37
    • 33645801996 scopus 로고    scopus 로고
    • 2, 5mol-%) resulted only in partial decomposition after 2 d at room temp., recovering starting 2g in 84% yield. The use of AgOTf (5 mol-%) instead resulted in diminished conversion (22% of 3g for 4 h at room temp.). For examples of the catalytic activity of both gold and protons, see: A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blacko, Adv. Synth. Catal. 2006, 348, 705-708.
    • 2, 5mol-%) resulted only in partial decomposition after 2 d at room temp., recovering starting 2g in 84% yield. The use of AgOTf (5 mol-%) instead resulted in diminished conversion (22% of 3g for 4 h at room temp.). For examples of the catalytic activity of both gold and protons, see: A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blacko, Adv. Synth. Catal. 2006, 348, 705-708.
  • 38
    • 34447507049 scopus 로고    scopus 로고
    • The double bond geometry was based on NOE experiments. See Supporting Information
    • The double bond geometry was based on NOE experiments. See Supporting Information.
  • 39
    • 9444284312 scopus 로고    scopus 로고
    • Antioxyauration of alkynes: a A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394.
    • Antioxyauration of alkynes: a) A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394.
  • 40
    • 0008279550 scopus 로고    scopus 로고
    • In a closely related cyclization of N-carbethoxy N-allyl propargylamine promoted by I2/AgBF4, a similar (Z/E) isomerization was noted, see: b) T. F. Tam, E. Thomas, A. Krantz, Tetrahedron Lett. 1987, 28, 1127-1130
    • 4, a similar (Z/E) isomerization was noted, see: b) T. F. Tam, E. Thomas, A. Krantz, Tetrahedron Lett. 1987, 28, 1127-1130.
  • 41
    • 0033524896 scopus 로고    scopus 로고
    • Isolation: a H. Kakeya, M. Morishita, H. Koshino, T.-L. Morita, K. Kobayashi, H. Osada, J. Org. Chem. 1999, 64, 1052-1053.
    • Isolation: a) H. Kakeya, M. Morishita, H. Koshino, T.-L. Morita, K. Kobayashi, H. Osada, J. Org. Chem. 1999, 64, 1052-1053.
  • 42
    • 24944550530 scopus 로고    scopus 로고
    • Synthesis: b J. D. Kim, I. S. Kim, C. H. Jin, O. P. Zee, Y. H. Jung, Org. Lett. 2005, 7, 4025-4028 and references cited therein.
    • Synthesis: b) J. D. Kim, I. S. Kim, C. H. Jin, O. P. Zee, Y. H. Jung, Org. Lett. 2005, 7, 4025-4028 and references cited therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.