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Volumn 4, Issue 15, 2002, Pages 2589-2592

BINOLAM, a recoverable chiral ligand for bifunctional enantioselective catalysis: The asymmetric synthesis of cyanohydrins

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; BINAP, 2 NAPHTHOL; BINAP, 2-NAPHTHOL; CYANOHYDRIN; ENZYME; LIGAND; NAPHTHALENE DERIVATIVE; NITRILE;

EID: 1642466422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0262338     Document Type: Article
Times cited : (122)

References (41)
  • 1
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    • For a recent review, see: Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
    • (2001) Tetrahedron , vol.57 , pp. 1865-1882
    • Rowlands, G.J.1
  • 18
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    • Diethylamino-substituted (S)- and (R)-BINOLAM 2 were the most suitable phase-transfer catalysts for the enantioselective alkylation of the aldimine Schiff bases of alanine esters: Casas, J.; Nájera, C.; Sansano, J. M.; González, J.; Saá, J. M.; Vega, M. Tetrahedron: Asymmetry 2001, 12, 699-702. For addition of diethylzinc to aldehydes, see: Kitajima, H.; Iti, K.; Katsuki, T. Chem. Lett. 1996, 343-344.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 699-702
    • Casas, J.1    Nájera, C.2    Sansano, J.M.3    González, J.4    Saá, J.M.5    Vega, M.6
  • 19
    • 0030522386 scopus 로고    scopus 로고
    • Diethylamino-substituted (S)- and (R)-BINOLAM 2 were the most suitable phase-transfer catalysts for the enantioselective alkylation of the aldimine Schiff bases of alanine esters: Casas, J.; Nájera, C.; Sansano, J. M.; González, J.; Saá, J. M.; Vega, M. Tetrahedron: Asymmetry 2001, 12, 699-702. For addition of diethylzinc to aldehydes, see: Kitajima, H.; Iti, K.; Katsuki, T. Chem. Lett. 1996, 343-344.
    • (1996) Chem. Lett. , pp. 343-344
    • Kitajima, H.1    Iti, K.2    Katsuki, T.3
  • 20
    • 49349140390 scopus 로고
    • BINOLAM 3 was easily prepared from methyl 3-hydroxy-2-naphthalenecarboxylate employing a chemical resolution using L-leucine methyl ester hydrochloride following a known procedure, (a) Feringa, B.; Wynberg, H. Tetrahedron Lett. 1977, 4447-4450.
    • (1977) Tetrahedron Lett. , pp. 4447-4450
    • Feringa, B.1    Wynberg, H.2
  • 27
    • 0037134213 scopus 로고    scopus 로고
    • Enantiopure cyanohydrins are important building blocks for the synthesis of 1,2-bifunctional compounds such as α-hydroxycarbonyl compounds, β-amino alcohols, and α-amino acids and also for the generation of new materials: (a) Liang, S.; Bu, X. R. J. Org. Chem. 2002, 67, 2702-2708.
    • (2002) J. Org. Chem. , vol.67 , pp. 2702-2708
    • Liang, S.1    Bu, X.R.2
  • 31
    • 84872268138 scopus 로고
    • Collins, A. N., Schedrake, G. N., Crosby, J., Eds.; Wiley: Chichester, UK, Chapter 14
    • (e) Kruse, C. G. In Chirality in Industry; Collins, A. N., Schedrake, G. N., Crosby, J., Eds.; Wiley: Chichester, UK, 1992; Chapter 14.
    • (1992) Chirality in Industry
    • Kruse, C.G.1
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    • (f) North, M. Synlett 1993, 807-820.
    • (1993) Synlett , pp. 807-820
    • North, M.1
  • 33
    • 84872277271 scopus 로고    scopus 로고
    • note
    • Thermogravimetric analysis of "dry" MS (dried at 120 °C for 4 h) revealed a 7.5% water content.
  • 35
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    • 3PO on prevention of oligomerization of the catalyst and activation of trimethylsilyl cyanide has been pointed out: Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570-1577.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1570-1577
    • Vogl, E.M.1    Gröger, H.2    Shibasaki, M.3
  • 41
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    • note
    • 4), and evaporated, affording a residue that was purified by flash chromatography to obtain pure cyanohydrins 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.