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Volumn 38, Issue 21, 1999, Pages 3186-3189

Facile, novel methodology for the synthesis of spiro[pyrrolidin-3,3'- oxindoles]: Catalyzed ring expansion reactions of cyclopropanes by aldimines

Author keywords

Alkaloids; Cyclopropanes; Nucleophilic additions; Ring expansions; Spiro compounds

Indexed keywords

ALKALOID; CYCLOPROPANE; PYRROLIDINE DERIVATIVE;

EID: 0033517689     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO;2-E     Document Type: Article
Times cited : (265)

References (36)
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    • Overman et al. have developed a novel approach to the catalytic, asymmetric synthesis of spiro oxindoles utilizing Heck reactions of unsaturated haloanilides; for a leading reference, see: A. Ashimori, B. Bachand, L. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6477
    • Ashimori, A.1    Bachand, B.2    Overman, L.3    Poon, D.J.4
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    • a) S. D. Edmonson, S. J. Danishefsky, Angew. Chem. 1998, 110, 1190; Angew. Chem. Int. Ed. 1998, 37, 1138;
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    • For an excellent review, see: a) E. D. Cox, J. Cook, Chem. Rev. 1995, 95, 1797; b) J. E. Saxton, Nat. Prod. Rep. 1997, 559.
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    • Cox, E.D.1    Cook, J.2
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    • 4243241249 scopus 로고    scopus 로고
    • For an excellent review, see: a) E. D. Cox, J. Cook, Chem. Rev. 1995, 95, 1797; b) J. E. Saxton, Nat. Prod. Rep. 1997, 559.
    • (1997) Nat. Prod. Rep. , pp. 559
    • Saxton, J.E.1
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    • For a discussion of charge affinity patterns and retrosynthetic analysis, see: D. A. Evans, G. C. Andrews, Acc. Chem. Res. 1974, 7, 147.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 147
    • Evans, D.A.1    Andrews, G.C.2
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    • The reactivity cyclopropanes towards nucleophiles is typically limited to those activated by two election-withdrawing groups or those that are highly strained. Exceptions to this generalization occur with strong nucleophiles such as metal selenides and Ni-catalyzed additions of organolaluminum compounds, see: a) A.B. Smith, R. M. Scarborough, Jr., Tetrahedron Lett. 1978, 1649; b) L. Bagnell, A. Meisters, T. Mole, Aust. J. Chem. 1975, 28, 821.
    • (1978) Tetrahedron Lett. , pp. 1649
    • Smith, A.B.1    Scarborough R.M., Jr.2
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    • The reactivity cyclopropanes towards nucleophiles is typically limited to those activated by two election-withdrawing groups or those that are highly strained. Exceptions to this generalization occur with strong nucleophiles such as metal selenides and Ni-catalyzed additions of organolaluminum compounds, see: a) A.B. Smith, R. M. Scarborough, Jr., Tetrahedron Lett. 1978, 1649; b) L. Bagnell, A. Meisters, T. Mole, Aust. J. Chem. 1975, 28, 821.
    • (1975) Aust. J. Chem. , vol.28 , pp. 821
    • Bagnell, L.1    Meisters, A.2    Mole, T.3
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    • It is important to note that in the absence of added metal salts, no reaction was observed
    • It is important to note that in the absence of added metal salts, no reaction was observed.
  • 36
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    • In this context, we have shown that the p-tolylsulfonyl protecting group could be removed in good yields (Na/naphthalene, THF, -100°C, 68% yield)
    • In this context, we have shown that the p-tolylsulfonyl protecting group could be removed in good yields (Na/naphthalene, THF, -100°C, 68% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.