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Volumn 52, Issue 9, 2011, Pages 987-991

Novel chiral hydrogen bond donor catalysts based on a 4,5-diaminoxanthene scaffold: Application to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes

Author keywords

Asymmetric synthesis; Bifunctional catalyst; Conjugate addition; Hydrogen bond donor catalyst; Organocatalyst; Xanthene scaffold

Indexed keywords

4,5 DIAMINO 9,9' DIMETHYLXANTHENE; ALKENE DERIVATIVE; AMINO ACID; CARBANILAMIDE; CARBONYL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; NUCLEOPHILE; PHENYLALANINE; PROLINE; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

EID: 79251598107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.067     Document Type: Article
Times cited : (16)

References (50)
  • 11
    • 0035799157 scopus 로고    scopus 로고
    • For reviews on the multimetallic bifunctional asymmetric catalysis, see: G.J. Rowlands Tetrahedron 57 2001 1865
    • (2001) Tetrahedron , vol.57 , pp. 1865
    • Rowlands, G.J.1
  • 15
    • 37649020600 scopus 로고    scopus 로고
    • Compound 2 was obtained in 75% yield, accompanied by formation of the di-Boc derivative (11%) and the recovery of 1 (10%). The di-Boc derivative was easily transformed into 1 in quantitative yield under basic conditions. For a reference of selective protection of 4,5-diamino-9,9-dimethylxanthenes, see: F.M. Muniz, L. Simón, S. Sáez, C. Raposo, and J.R. Morán Tetrahedron Lett. 49 2007 790
    • (2007) Tetrahedron Lett. , vol.49 , pp. 790
    • Muniz, F.M.1    Simón, L.2    Sáez, S.3    Raposo, C.4    Morán, J.R.5
  • 16
    • 79251601165 scopus 로고    scopus 로고
    • Partial racemization occurred when N,N-dimethyl (S)-phenylalanine was directly utilized for the coupling reaction
    • Partial racemization occurred when N,N-dimethyl (S)-phenylalanine was directly utilized for the coupling reaction.
  • 17
    • 0142072631 scopus 로고    scopus 로고
    • Precedent examples of asymmetric conjugate addition of acetylacetone and malonate nucleophiles to nitroalkenes. Asymmetric organocatalysis: T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672
    • Okino, T.1    Hoashi, Y.2    Takemoto, Y.3
  • 31
    • 0035905575 scopus 로고    scopus 로고
    • For reviews on catalytic asymmetric construction of a quaternary stereocenter, see: J. Christffer, and A. Mann Angew. Chem., Int. Ed. 40 2001 4591
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4591
    • Christffer, J.1    Mann, A.2
  • 35
    • 11844302258 scopus 로고    scopus 로고
    • Precedent examples of asymmetric conjugate addition of 1,3-diketones to nitroalkenes to construct an all-carbon quaternary carbon center: T. Okino, Y. Hoashi, T. Furukawa, X. Xu, and Y. Takemoto J. Am. Chem. Soc. 127 2005 119
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 119
    • Okino, T.1    Hoashi, Y.2    Furukawa, T.3    Xu, X.4    Takemoto, Y.5
  • 39
    • 79251599099 scopus 로고    scopus 로고
    • See also Refs. 8d,e,g,j
    • See also Refs. 8d,e,g,j
  • 47
    • 79251599150 scopus 로고    scopus 로고
    • No reaction occurred when 2-acetylcyclohexanone was used as the nucleophile
    • No reaction occurred when 2-acetylcyclohexanone was used as the nucleophile.
  • 48
    • 79251593517 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of acetylacetone to 6a using (S)-proline-derived catalyst 5m gave (R)-7a in 65% yield with 71% ee (4 °C, 96 h), analogous to the case of (S)-phenylalanine-derived catalyst 5d (Table 1, entry 4)
    • Asymmetric conjugate addition of acetylacetone to 6a using (S)-proline-derived catalyst 5m gave (R)-7a in 65% yield with 71% ee (4 °C, 96 h), analogous to the case of (S)-phenylalanine-derived catalyst 5d (Table 1, entry 4).
  • 49
    • 84962467066 scopus 로고    scopus 로고
    • Another possibility that 1,3-dicarbonyl compounds interact with the urea catalyst based on a 4,5-diaminoxanthene scaffold through multiple hydrogen bonds would not be excluded at the present stage. For the theoretical studies of the mode of interaction between bifunctional thiourea derivatives and 1,3-dicarbonyl compounds in asymmetric conjugate addition to nitroalkenes, see: A. Hamza, G. Schubert, T. Soóe, and I. Pápai J. Am. Chem. Soc. 128 2006 13151 See also reference 11f
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 13151
    • Hamza, A.1    Schubert, G.2    Soóe, T.3    Pápai, I.4
  • 50
    • 79251596510 scopus 로고    scopus 로고
    • At the present stage, the origin of enantiofacial discrimination of the prochiral enolate is unknown
    • At the present stage, the origin of enantiofacial discrimination of the prochiral enolate is unknown.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.