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Volumn 44, Issue 28, 2003, Pages 5285-5288

A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

Author keywords

[No Author keywords available]

Indexed keywords

BORON; BORON DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; CHROMANE CARBOXYLATE; DIISOPINOCAMPHEYLBORON ENOLATE; ESTER DERIVATIVE; LIGAND; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; REAGENT; UNCLASSIFIED DRUG;

EID: 0038684476     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01220-6     Document Type: Article
Times cited : (12)

References (21)
  • 1
    • 0034678591 scopus 로고    scopus 로고
    • Recent reviews on asymmetric aldol reactions: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352; (b) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917; (c) Carreira, E. M. Chapter 29 from 'Comprehensive Asymmetric Catalysis', E. N. Jacobsen, Ed.; 1999, pp. 998-1065; (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1352
    • Machajewski, T.D.1    Wong, C.-H.2
  • 2
    • 0034635481 scopus 로고    scopus 로고
    • Recent reviews on asymmetric aldol reactions: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352; (b) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917; (c) Carreira, E. M. Chapter 29 from 'Comprehensive Asymmetric Catalysis', E. N. Jacobsen, Ed.; 1999, pp. 998-1065; (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
    • (2000) Tetrahedron , vol.56 , pp. 917
    • Arya, P.1    Qin, H.2
  • 3
    • 0000699983 scopus 로고    scopus 로고
    • E. N. Jacobsen, Ed.
    • Recent reviews on asymmetric aldol reactions: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352; (b) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917; (c) Carreira, E. M. Chapter 29 from 'Comprehensive Asymmetric Catalysis', E. N. Jacobsen, Ed.; 1999, pp. 998-1065; (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
    • (1999) Chapter 29 from 'Comprehensive Asymmetric Catalysis' , pp. 998-1065
    • Carreira, E.M.1
  • 4
    • 0032512595 scopus 로고    scopus 로고
    • Recent reviews on asymmetric aldol reactions: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352; (b) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917; (c) Carreira, E. M. Chapter 29 from 'Comprehensive Asymmetric Catalysis', E. N. Jacobsen, Ed.; 1999, pp. 998-1065; (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357
    • Nelson, S.G.1
  • 8
    • 0028853930 scopus 로고
    • Bernardi A., Gennari C., Goodman J.M., Paterson I. Tetrahedron: Asymmetry. 6:1995;2613 Kim, B. M.; Williams, S. F.; Masamune, S. Comprehensive Org. Syn.; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p. 239 Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochem.; Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; John Wiley & Sons: New York, 1982; Vol. 13, p. 1 and references cited therein.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2613
    • Bernardi, A.1    Gennari, C.2    Goodman, J.M.3    Paterson, I.4
  • 15
    • 85031154264 scopus 로고    scopus 로고
    • For use as LTD4 inhibitors: European Patent, Masateru, M. et al. 1990, EP150447; US patents: Masateru, M. et al. US 4665203; Masateru, M. et al. US 4778903; Masateru, M. et al. US 4888356; Masateru, M. et al. US 4952705; and Cohen N. et al. J. Med. Chem. 1989, 32, 1842 For use as PPAR agonists: US patent: Sahoo, S. P. et al. US 2002/0103242; World patent: Sahoo, S. P. et al. WO 02/26729 For antioxidants/antiarrhythmic activity: US patent: Scott, J. W. et al. 1977, US 4018799, Scott, J. W. et al. 1977, US 4003919, Scott, J. W. et al. 1977, US 4026907; World patent: Koufaki, M. et al. 2002, WO 02/04438.
  • 19
    • 85031158746 scopus 로고    scopus 로고
    • note
    • Various methods were explored for the chiral aldol reaction with limited success before we discovered the boron-mediated aldol reaction, which gave far superior results. The methods investigated included chiral Lewis acid-catalyzed Mukaiyama type aldol through silyl ketene acetal 7 and chiral aldol reaction of Zn-enolate with chiral diamine or aminoalcohol ligands etc.
  • 20
    • 85031145057 scopus 로고    scopus 로고
    • note
    • 14.
  • 21
    • 85031150710 scopus 로고    scopus 로고
    • note
    • 4Na (M+Na): 287.1254. Found 287.1264. 19, 14 and 15, aldol reaction of 16 gave ca. 50% yield with modest selectivity: dr=7 and 45% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.