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Volumn 65, Issue 15, 2000, Pages 4593-4600

Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans,trans-2,4-disubstituted pyrrolidine-3-carboxylates

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHYLENE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE;

EID: 0034725813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000206i     Document Type: Article
Times cited : (44)

References (33)
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    • (f) Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826-827. Reviews: Revial, G.; Pfau, M. Org. Synth. 1991, 70, 35-46. Oare, D. A.; Heathcock, C. H. Topics Stereochem. 1991, 20, 87-170 (see p 114). D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. D'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555-616. Guingant, A. Advances in Asymmetric Synthesis; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 159-174. Developments and applications: Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references included.
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    • (f) Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826-827. Reviews: Revial, G.; Pfau, M. Org. Synth. 1991, 70, 35-46. Oare, D. A.; Heathcock, C. H. Topics Stereochem. 1991, 20, 87-170 (see p 114). D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. D'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555-616. Guingant, A. Advances in Asymmetric Synthesis; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 159-174. Developments and applications: Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references included.
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    • 0031040549 scopus 로고    scopus 로고
    • (f) Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826-827. Reviews: Revial, G.; Pfau, M. Org. Synth. 1991, 70, 35-46. Oare, D. A.; Heathcock, C. H. Topics Stereochem. 1991, 20, 87-170 (see p 114). D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. D'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555-616. Guingant, A. Advances in Asymmetric Synthesis; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 159-174. Developments and applications: Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references included.
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    • 0031040549 scopus 로고    scopus 로고
    • JAI Press Inc.: Greenwich, CT
    • (f) Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826-827. Reviews: Revial, G.; Pfau, M. Org. Synth. 1991, 70, 35-46. Oare, D. A.; Heathcock, C. H. Topics Stereochem. 1991, 20, 87-170 (see p 114). D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. D'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555-616. Guingant, A. Advances in Asymmetric Synthesis; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 159-174. Developments and applications: Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references included.
    • (1997) Advances in Asymmetric Synthesis , vol.2 , pp. 159-174
    • Guingant, A.1
  • 15
    • 0030939611 scopus 로고    scopus 로고
    • and references included
    • (f) Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826-827. Reviews: Revial, G.; Pfau, M. Org. Synth. 1991, 70, 35-46. Oare, D. A.; Heathcock, C. H. Topics Stereochem. 1991, 20, 87-170 (see p 114). D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. D'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555-616. Guingant, A. Advances in Asymmetric Synthesis; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 159-174. Developments and applications: Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references included.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1101-1109
    • Jabin, I.1    Revial, G.2    Melloul, K.3    Pfau, M.4
  • 19
    • 0033612169 scopus 로고    scopus 로고
    • Recently, the reaction displayed in Scheme 1 was extended to the reaction of cyclohexanones imines with 2-substituted nitroethylenes, affording tetrahydroindoles: Lim. S.; Jabin, I.; Revial, G. Tetrahedron Lett. 1999, 40, 4177-4180.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4177-4180
    • Lim, S.1    Jabin, I.2    Revial, G.3
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    • note
    • Optimized molecular structures were generated using the combination of CS Chemdraw Pro 5.0 (1998) and CS Chem3D Pro 5.0 (1999), Cambridge Soft (Cambridge, MA). The resulting MM2 geometries were refined with the semiempirical molecular orbital PM3 algorithm available in CS Mopac Pro.
  • 31
    • 0343566966 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of compound 43.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.