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Volumn 54, Issue 7, 1998, Pages 1221-1232

Diastereocontrolled synthesis of pyrrolidines by nickel promoted tandem cyclization-quenching of aminobromodienes

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL; PYRROLIDINE DERIVATIVE;

EID: 0032510203     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10220-4     Document Type: Article
Times cited : (24)

References (30)
  • 4
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    • 4. For a review on the use of aminoacid and derivatives thereof in asymmetric synthesis, see: Ager, D. A.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
    • (1996) Chem. Rev. , vol.96 , pp. 835-875
    • Ager, D.A.1    Prakash, I.2    Schaad, D.R.3
  • 5
    • 0010662182 scopus 로고    scopus 로고
    • note
    • 2CN moiety.
  • 6
    • 0029928957 scopus 로고    scopus 로고
    • 13CNMR could also be used as a diagnostic tool, since Δδ around 3 ppm were observed. For a related empirical use of chemical shift differences for stereochemical assignments in related compounds, see Hashimoto, K.; Konno, K.; Shirahama, H. J. Org. Chem. 1996, 61, 4685-4692.
    • (1996) J. Org. Chem. , vol.61 , pp. 4685-4692
    • Hashimoto, K.1    Konno, K.2    Shirahama, H.3
  • 8
    • 0001200603 scopus 로고
    • 8. In order to explain the high or complete diastereoselectivity observed for substrates bearing an ester (1g and 1h) or a carbamate group (1i) (entries 7-9, Table 1), an additional attractive interaction between the side chain carbonyl group and the nitrogen lone pair could also be considered. Attractive interaction N→C=O has been demonstrated both in solid state and in solution; see, for example: a) Schweizer, W.B.; Procter, G.; Kaftory, M.; Dunitz; J.D. Helv. Chim. Acta , 1978, 61, 2783-2808;
    • (1978) Helv. Chim. Acta , vol.61 , pp. 2783-2808
    • Schweizer, W.B.1    Procter, G.2    Kaftory, M.3    Dunitz, J.D.4
  • 11
    • 0031575584 scopus 로고    scopus 로고
    • and references cited therein. Additional examples where this type of interaction has also been invoked: Selectivity control in Diels-Alder reactions
    • d) Leonard, N.J. Tetrahedron., 1997, 53, 2325-2355 and references cited therein. Additional examples where this type of interaction has also been invoked: Selectivity control in Diels-Alder reactions:
    • (1997) Tetrahedron , vol.53 , pp. 2325-2355
    • Leonard, N.J.1
  • 14
    • 0000377497 scopus 로고
    • Conformational equilibrium related to bioactivity of certain analgesics
    • g) Bachrach, S.M. J. Org. Chem. 1995, 60, 4395-4398. Conformational equilibrium related to bioactivity of certain analgesics:
    • (1995) J. Org. Chem. , vol.60 , pp. 4395-4398
    • Bachrach, S.M.1
  • 15
    • 0015917659 scopus 로고
    • Correlation with the geometry of nucleophile approach on the attack to carbonyl or nitrile groups
    • h) Bürgi, H.B.; Dunitz, J.D.; Shefter, E. Nature new Biol., 1973, 244, 186-188. Correlation with the geometry of nucleophile approach on the attack to carbonyl or nitrile groups:
    • (1973) Nature New Biol. , vol.244 , pp. 186-188
    • Bürgi, H.B.1    Dunitz, J.D.2    Shefter, E.3
  • 20
    • 0010743779 scopus 로고    scopus 로고
    • note
    • 11. In agreement with our previous results, cyclization of 1k under standard conditions afforded a complex mixture in which no trace (formula presented) of the desired cycloadduct 2 could be detected. However, this result indicates the inability of the side chain acetate carbonyl group to stabilize by coordination an alkylnickel intermediate such as 2′ (see Figure 3).
  • 21
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    • 12. Although in 3c and in 3e, a vinylnickel-carbonyl coordination could be the origin of the diastereoselection, we have been unable to find a likely explanation for our experimental results based on this hypothesis. For coordination of carbonyl groups with the metal center in organometallic nickel compounds, see: a) Sacerdoti, M.; Bertolasi, V.; Gilli, G. Acta Crystallogr. 1980, B36, 1061;
    • (1980) Acta Crystallogr. , vol.B36 , pp. 1061
    • Sacerdoti, M.1    Bertolasi, V.2    Gilli, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.