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Volumn 5, Issue 10, 2003, Pages 1757-1760

Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMMONIUM DERIVATIVE; LITHIUM DERIVATIVE; OXAZOLIDINE DERIVATIVE; REAGENT; SIMMONS SMITH REAGENT; UNCLASSIFIED DRUG;

EID: 0141852823     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034404i     Document Type: Article
Times cited : (35)

References (34)
  • 2
    • 0000033512 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY
    • For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
    • (1991) Comprehensive Organic Synthesis , pp. 913
    • Markó, I.E.1
  • 3
    • 0001485086 scopus 로고    scopus 로고
    • For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
    • (1997) Chem. Rev. , vol.97 , pp. 2341
    • Aggarwal, V.K.1    Li, A.H.2    Dai, L.X.3
  • 10
    • 0037460171 scopus 로고    scopus 로고
    • Allylic amines bearing a non-nucleophilic nitrogen readily undergo cyclopropanation with the Simmons-Smith reagent; see: Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 761
    • Wipf, P.1    Kendall, C.2    Stephenson, C.R.J.3
  • 17
    • 0141550141 scopus 로고    scopus 로고
    • note
    • We have tried MeONa and pseudo-ephedrine salts made from 1 equiv of (1R,2R)-pseudo-ephedrine/1 equiv of LiHMDS or NaHMDS and 1 equiv of (1R,2R)-pseudo-ephendrine/2 equiv of n-BuLi as additives in THF solution at 0°C. In all cases, no neutral amines were obtained after workup.
  • 25
    • 0028911643 scopus 로고
    • For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2519
    • Clark, J.S.1    Hodgson, P.B.2
  • 26
    • 0029930972 scopus 로고    scopus 로고
    • For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2165
    • Wright, D.L.1    Weekly, R.M.2    Groff, R.3    McMills, M.C.4
  • 27
    • 0001131525 scopus 로고
    • For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
    • (1978) J. Org. Chem. , vol.43 , pp. 1185
    • Vedejs, E.1    Hagen, J.P.2    Roach, B.L.3    Spear, K.L.4
  • 28
    • 0141438612 scopus 로고    scopus 로고
    • note
    • For another example in which one diastereoisomer of an ylide undergoes [2,3] rearrangement and the other diastereomer undergoes a [1,2] rearrangement, see ref 18b.
  • 29
    • 33846971478 scopus 로고
    • Ylide 15 would not be expected to undergo Stevens rearrangement, as [2,3] sigmatropic rearrangements are generally faster processes than [1,2] rearrangements. Mageswaran, S.; Ollis, W. D.; Sutherland, I. O.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun. 1971, 1494. For a review on Stevens rearrangements, see ref 2.
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 1494
    • Mageswaran, S.1    Ollis, W.D.2    Sutherland, I.O.3    Thebtaranonth, Y.4
  • 32
    • 0000017190 scopus 로고
    • For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
    • (1984) J. Org. Chem. , vol.49 , pp. 1917
    • Doyle, M.P.1    Griffin, J.H.2    Chinn, M.S.3    Leusen, D.V.4
  • 33
    • 0031597451 scopus 로고    scopus 로고
    • For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
    • (1998) Synthesis , pp. 653
    • Trauner, D.1    Porth, S.2    Opatz, T.3    Bats, J.W.4    Giester, G.5    Mülzer, J.6
  • 34
    • 0029904822 scopus 로고    scopus 로고
    • For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1970
    • Mülzer, J.1    Trauner, D.2    Bats, J.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.