메뉴 건너뛰기




Volumn 48, Issue 48, 2007, Pages 8521-8525

Synthesis of new chiral cyclic 1,2-diamines and their evaluation as catalysts for enantioselective Diels-Alder reactions

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; CYCLIC 1,2 DIAMINE DERIVATIVE; DIAMINE DERIVATIVE; DICARBOXYLIC ACID; UNCLASSIFIED DRUG; ZINC;

EID: 35548980803     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.149     Document Type: Article
Times cited : (20)

References (33)
  • 8
    • 33846957747 scopus 로고    scopus 로고
    • For some recent contributions see for example: and references cited there
    • For some recent contributions see for example:. Liu Y., Melgar-Fernandez R., and Juaristi E. J. Org. Chem. 72 (2007) 1522-1525 and references cited there
    • (2007) J. Org. Chem. , vol.72 , pp. 1522-1525
    • Liu, Y.1    Melgar-Fernandez, R.2    Juaristi, E.3
  • 10
    • 33847793920 scopus 로고    scopus 로고
    • and references cited there
    • McCooey S.H., and Connon S.J. Org. Lett. 9 (2007) 599-602 and references cited there
    • (2007) Org. Lett. , vol.9 , pp. 599-602
    • McCooey, S.H.1    Connon, S.J.2
  • 12
    • 20144383282 scopus 로고    scopus 로고
    • For 1,2-diaminocyclohexane-derived salen ligands see:
    • For 1,2-diaminocyclohexane-derived salen ligands see:. McGarrigle E.M., and Gilheany D.G. Chem. Rev. 105 (2005) 1563-1602
    • (2005) Chem. Rev. , vol.105 , pp. 1563-1602
    • McGarrigle, E.M.1    Gilheany, D.G.2
  • 15
    • 33947137197 scopus 로고    scopus 로고
    • For other 1,2-diaminocyclohexane-derived ligands see:
    • For other 1,2-diaminocyclohexane-derived ligands see:. Colombo F., Annunziata R., and Benaglia M. Tetrahedron Lett. 48 (2007) 2687-2690
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2687-2690
    • Colombo, F.1    Annunziata, R.2    Benaglia, M.3
  • 16
    • 3042550754 scopus 로고    scopus 로고
    • For 1,2-diphenylethylene diamine ligands see Ref.3 and and references cited there
    • For 1,2-diphenylethylene diamine ligands see Ref.3 and. Hamada T., Manabe K., and Kobayashi S. J. Am. Chem. Soc. 126 (2004) 7768-7769 and references cited there
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 7768-7769
    • Hamada, T.1    Manabe, K.2    Kobayashi, S.3
  • 17
    • 33745683612 scopus 로고    scopus 로고
    • See also and references cited there
    • See also. Park B.-M., Mun S., and Yun J. Adv. Synth. Catal. 348 (2006) 1029-1032 and references cited there
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 1029-1032
    • Park, B.-M.1    Mun, S.2    Yun, J.3
  • 25
    • 35548930431 scopus 로고    scopus 로고
    • note
    • 3 sat. sol. and filtered; ethylacetate was added and the two phases were separated and the organic phase extracted twice with ethylacetate, dried over sodium sulfate and filtered before removal of the solvent under reduced pressure. If necessary, the products were purified by flash chromatography on a short silica gel column with ethylacetate/hexane mixture as eluant.
  • 26
    • 35548975354 scopus 로고    scopus 로고
    • note
    • 2: C, 81,76; H, 10,29; N, 7,95. Found: C, 81.77; H, 10.31; N, 7.91.
  • 27
    • 0037139610 scopus 로고    scopus 로고
    • For highly enantioselective Diels-Alder reactions promoted by chiral secondary amines see: and references cited there
    • For highly enantioselective Diels-Alder reactions promoted by chiral secondary amines see:. Northrup A.B., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 2458-2460 and references cited there
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2458-2460
    • Northrup, A.B.1    MacMillan, D.W.C.2
  • 28
    • 35548957049 scopus 로고    scopus 로고
    • note
    • 4 reduction of the adducts 14 (see tables for analysis conditions).
  • 29
    • 35549013458 scopus 로고    scopus 로고
    • note
    • For a recent work employing a monosalt of a diaminic substrate see Ref. 7b.
  • 30
    • 0034600250 scopus 로고    scopus 로고
    • For the use of water as additive in some organocatalyzed reactions see for example:
    • For the use of water as additive in some organocatalyzed reactions see for example:. Ahrendt K.A., Borths C.J., and MacMillan D.W.C. J. Am. Chem. Soc. 122 (2000) 4243-4244
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4243-4244
    • Ahrendt, K.A.1    Borths, C.J.2    MacMillan, D.W.C.3
  • 32
    • 35548955254 scopus 로고    scopus 로고
    • note
    • More bulky N-substituted alkyl amines (e.g., the N-isopentyl derivative) did not promote the reaction in appreciable yields.
  • 33
    • 35548946839 scopus 로고    scopus 로고
    • note
    • 2-symmetry of the uncoordinated ligand. The catalytic ability of such chiral organometallic species is currently under active investigation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.