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Volumn , Issue 6, 2007, Pages 893-896

Controlling diastereoselectivity in the tandem microwave-assisted aza-Cope rearrangement-Mannich cyclization

Author keywords

Amino alcohols; Cyclizations; Diastereoselectivity; Rearrangements; Tandem reactions

Indexed keywords

PYRROLIDINE DERIVATIVE;

EID: 34247167569     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973878     Document Type: Article
Times cited : (12)

References (44)
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    • For reviews of tandem or domino reactions, see: a
    • For reviews of tandem or domino reactions, see: (a) Pellissier, H. Tetrahedron 2006, 62, 1619.
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    • For reviews of the aza-Cope rearrangement-Mannich cyclization and related reactions, see: a
    • For reviews of the aza-Cope rearrangement-Mannich cyclization and related reactions, see: (a) Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
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    • Bonin, M.1    Micouin, L.2
  • 10
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    • Aza-Cope-Mannich reactions have also been initiated by elimination of a leaving group to form the iminium cation. See, for example: (a) Overman, L. E, Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741
    • Aza-Cope-Mannich reactions have also been initiated by elimination of a leaving group to form the iminium cation. See, for example: (a) Overman, L. E.; Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741.
  • 19
    • 29844435276 scopus 로고    scopus 로고
    • For recent applications of the aza-Cope rearrangement-Mannich cyclization in the synthesis of natural products, see: (a) Earley, W. G, Jacobsen, J. E, Madlin, A, Meier, G. P, O'Donnell, C. J, Oh, T, Old, D. W, Overman, L. E, Sharp, M. J. J. Am. Chem. Soc. 2005, 127, 18046
    • For recent applications of the aza-Cope rearrangement-Mannich cyclization in the synthesis of natural products, see: (a) Earley, W. G.; Jacobsen, J. E.; Madlin, A.; Meier, G. P.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 2005, 127, 18046.
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    • For reviews, see: a
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    • For books, see: a, Tierney, J. P, Lidstrom, P, Eds, Blackwell: Oxford
    • For books, see: (a) Microwave Assisted Organic Synthesis; Tierney, J. P.; Lidstrom, P., Eds.; Blackwell: Oxford, 2005.
    • (2005) Microwave Assisted Organic Synthesis
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    • (c) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2006.
    • (2006) Microwaves in Organic Synthesis
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    • For reviews, see: a
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    • For examples of imine or iminium cation formation using microwave-assisted methods, see: (a) Shi, L, Tu, Y.-Q, Wang, M, Zhang, F.-M, Fan, C.-A. Org. Lett. 2004, 6, 1001
    • For examples of imine or iminium cation formation using microwave-assisted methods, see: (a) Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A. Org. Lett. 2004, 6, 1001.
  • 41
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    • Relative stereochemistry was confirmed by NOE analysis of 10b. MeMgBr addition to 9a and 9b followed by benzyl or benzhydryl deprotection yielded the same pyrrolidine.
    • Relative stereochemistry was confirmed by NOE analysis of 10b. MeMgBr addition to 9a and 9b followed by benzyl or benzhydryl deprotection yielded the same pyrrolidine.
  • 42
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    • For an excellent discussion of the possible pathways for erosion of stereoselectivity in the aza-Cope-Mannich reaction, see ref. 4d
    • For an excellent discussion of the possible pathways for erosion of stereoselectivity in the aza-Cope-Mannich reaction, see ref. 4d
  • 43
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    • For reviews of allylic strain-directed reactions, see: a
    • For reviews of allylic strain-directed reactions, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
    • (1993) Chem. Rev , vol.93 , pp. 1307
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.