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Volumn , Issue 1, 2006, Pages 133-136

Phosphorodiamidic acid as a novel structural motif of Brønsted acid catalysts for direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds

Author keywords

Asymmetric catalysis; Green chemistry; Imines; Mannich reaction; Organocatalyst

Indexed keywords

ACID; BRONSTED ACID; CARBONYL DERIVATIVE; IMINE; NAPHTHALENE DERIVATIVE; NITROGEN; PHOSPHORODIAMIDIC ACID; PHOSPHORUS DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 30544448390     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922783     Document Type: Article
Times cited : (86)

References (69)
  • 1
    • 0026418434 scopus 로고
    • Reviews on atom economy: (a) Trost, B. M. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 5
    • 30544450304 scopus 로고    scopus 로고
    • Organic catalysis
    • Special issue
    • (b) Special issue on Organic Catalysis': Adv. Synth. Catal. 2004, 346.
    • (2004) Adv. Synth. Catal. , pp. 346
  • 6
    • 33746276615 scopus 로고    scopus 로고
    • Enantioselective organocatalysis
    • Special issue
    • (c) Special issue on 'Enantioselective Organocatalysis': Acc. Chem. Res. 2004, 37.
    • (2004) Acc. Chem. Res. , pp. 37
  • 10
    • 0346865819 scopus 로고    scopus 로고
    • For reviews on Brønsted acid catalysis, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 289
    • Schreiner, P.R.1
  • 25
    • 0003441992 scopus 로고    scopus 로고
    • Yamamoto, H., Ed.; Wiley-VCH: Weinheim
    • (b) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000.
    • (2000) Lewis Acids in Organic Synthesis
  • 31
  • 33
    • 0000287240 scopus 로고    scopus 로고
    • and references therein
    • (a) Review: Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2581; and references therein,
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2581
  • 36
    • 30544441545 scopus 로고    scopus 로고
    • note
    • -: 477.0349. Found: 477.0351.
  • 37
    • 1642415515 scopus 로고    scopus 로고
    • (a) For an excellent review of organocatalytic asymmetric direct Mannich reactions, see: Cordova, A. Acc. Chem. Res. 2004, 37, 102. See also:
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102
    • Cordova, A.1
  • 39
    • 30544439716 scopus 로고    scopus 로고
    • See ref. 3d, Chapter 5.2
    • See ref. 3d, Chapter 5.2.
  • 52
    • 30544446431 scopus 로고    scopus 로고
    • note
    • 1H NMR. The percentages of the enol form are listed as follows: 3a: 72%; 3b: 61%; 3c: >98%; 3d: 6%; 3e: 6%; 3f: 21%; 3g: <2%.
  • 53
    • 30544443107 scopus 로고    scopus 로고
    • note
    • Although in the case of unsymmetrical 1,3-dicarbonyl compounds, keto esters 3d,e and keto amide 3f, the diastereomeric mixtures were obtained, their ratios were changed during the course of experiment.
  • 54
    • 0028070796 scopus 로고
    • For binaphthalene bis(sulfonamide) derivatives as a chiral ligand for metal-based catalysts, see: (a) Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6693
    • Terada, M.1    Motoyama, Y.2    Mikami, K.3
  • 62
    • 0141519439 scopus 로고    scopus 로고
    • For binaphthalene-derived diazaphosphepines as a chiral ligand for metal-based catalysts, see: (a) Reetz, M. T.; Oka, H.; Goddard, R. Synthesis 2003, 1809.
    • (2003) Synthesis , pp. 1809
    • Reetz, M.T.1    Oka, H.2    Goddard, R.3
  • 66
    • 30544439209 scopus 로고    scopus 로고
    • note
    • -: 653.0975. Found 653.0975.
  • 67
    • 30544440234 scopus 로고    scopus 로고
    • note
    • +: 332.1257. Found: 332.1260.
  • 68
    • 30544446770 scopus 로고    scopus 로고
    • note
    • The absolute configuration of Bz-product 4e was determined after transformation into the stereochemically known N-benzoylphenylglycine methyl ester. The stereochemical determination of 4a and the experimental procedure for derivatization of 4 to N-protected glycine methyl ester were described in ref. 8a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.