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Volumn , Issue 10, 2003, Pages 1993-2000

Solvent and temperature effects on diastereofacial selectivity: Amines as co-solvents in n-butyllithium addition to α-chiral aldehydes

Author keywords

Aldehydes; Amines; Entropy; Inversion temperature; Solvent effects; Solvent mixtures

Indexed keywords

ALDEHYDE; ALDEHYDE DERIVATIVE; ALIPHATIC HYDROCARBON; AMINE; HEXANE; LITHIUM DERIVATIVE; PHENYLPROPANOLAMINE; SOLVENT; TERTIARY AMINE;

EID: 0037573528     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200579     Document Type: Article
Times cited : (13)

References (51)
  • 19
    • 0025780257 scopus 로고
    • For a review see: H. Buschmann, H.-D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480; Angew. Chem. Int. Ed. Engl. 1991, 30, 477.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 477
  • 22
    • 0030500406 scopus 로고    scopus 로고
    • [9b] G. Cainelli, D. Giacomini, P. Galletti, A. Marini, Angew. Chem. 1996, 108, 3016; Angew. Chem. Int. Ed. Engl. 1996, 35, 2849.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2849
  • 24
    • 0034603102 scopus 로고    scopus 로고
    • G. Cainelli, D. Giacomini, P. Galletti, P. Orioli, Angew. Chem. 2000, 112, 533; Angew. Chem. Int. Ed. 2000, 39, 523.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 523
  • 25
    • 0342981459 scopus 로고    scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 381
    • Muzart, J.1    Hénin, F.2    Aboulhoda, S.J.3
  • 26
    • 0001580728 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9333
    • Palucki, M.1    Pospisil, P.J.2    Zhang, W.3    Jacobsen, E.N.4
  • 27
    • 0027930852 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1994) Tetrahedron , vol.50 , pp. 6819
    • Brunne, J.1    Hoffmann, N.2    Scharf, H.-D.3
  • 28
    • 0001050315 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1993) Angew. Chem. , vol.105 , pp. 1417
    • Göbel, T.1    Sharpless, K.B.2
  • 29
    • 33748671672 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1329
  • 30
    • 0027139307 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2531
    • Muzart, J.1    Hénin, F.2    Pète, J.-P.3    M'Boungou-M'Passi, A.4
  • 31
    • 4243796211 scopus 로고
    • [8] and: [11a] J. Muzart, F. Hénin, S. J. Aboulhoda, Tetrahedron: Asymmetry 1997, 8, 381. [11b] M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 9333. [11c] J. Brunne, N. Hoffmann, H.-D. Scharf, Tetrahedron 1994, 50, 6819. [11d] T. Göbel, K. B. Sharpless, Angew. Chem. 1993, 105, 1417; Angew. Chem. Int. Ed. Engl. 1993, 32, 1329. [11e] J. Muzart, F. Hénin, J.-P. Pète, A. M'boungou-M'Passi, Tetrahedron: Asymmetry 1993, 4, 2531. [11f] I. Tóth, I. Guo, B. E. Hanson, Organometallics 1993, 12, 477.
    • (1993) Organometallics , vol.12 , pp. 477
    • Tóth, I.1    Guo, I.2    Hanson, B.E.3
  • 41
    • 0037556110 scopus 로고    scopus 로고
    • note
    • inv we observed a large dispersion of data, whereas at all other selected temperatures anti/syn ratios are highly consistent with the linear trend.
  • 42
    • 0037894017 scopus 로고    scopus 로고
    • note
    • [2b]
  • 43
    • 0038570300 scopus 로고    scopus 로고
    • note
    • Experimental data of In(anti/syn) collected between - 19 and 0 °C differ from the theoretical median values calculated in this T range extrapolating the two extreme linear regions, thus giving evidence for the presence of a new different solvation species. Moreover, we do not observe any data scattering in this region.
  • 44
    • 0032540671 scopus 로고    scopus 로고
    • and references cited therein
    • D. Hoffmann, D. B. Collum, J Am. Chem. Soc. 1998, 120, 5810-5811 and references cited therein.
    • (1998) J Am. Chem. Soc. , vol.120 , pp. 5810-5811
    • Hoffmann, D.1    Collum, D.B.2
  • 47
    • 0037894016 scopus 로고    scopus 로고
    • note
    • [2b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.