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Volumn , Issue 30, 2009, Pages 5208-5214

Organocatalytic anti/-selective mannich reactions with fluorinated aldimines: synthesis of anti-γ-fluoroalkyl-γ-amino alcohols

Author keywords

Amino alcohols; Enantioselectivity; Fluorinated imines; Mannich reaction; Organocatalysis

Indexed keywords


EID: 70350192339     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900509     Document Type: Article
Times cited : (29)

References (57)
  • 38
    • 33644650296 scopus 로고    scopus 로고
    • For the synthesis of &-(trifluoromethyl)-β-amino acids through the Mannich-type reaction of chiral trifluoromethyl oxazolidines, see: F. Huguenot, T. Brigaud, J. Org. Chem. 2006, 71, 2159-2162.
    • (2006) J. Org. Chem. , vol.71 , pp. 2159-2162
    • Huguenot, F.1    Brigaud, T.2
  • 49
    • 33744826542 scopus 로고    scopus 로고
    • For the synthesis of nonfluorinated α- or β-unsubstituted γamino alcohols through Mannich reactions with catalysts 4, see: a) Y Chi, S. H. Gellman, J Am. Chem. Soc. 2006, 128, 6804-6805;
    • (2006) J Am. Chem. Soc. , vol.128 , pp. 6804-6805
    • Chi, Y.1    Gellman, S.H.2
  • 51
    • 51749084445 scopus 로고    scopus 로고
    • For a recent review on the use of diarylprolinol ethers as catalysts, see: A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922-948.
    • (2008) Chem. Asian J. , vol.3 , pp. 922-948
    • Mielgo, A.1    Palomo, C.2
  • 52
    • 53549103052 scopus 로고    scopus 로고
    • Catalysts 4 have been employed in the enantioselective a-iluorination of carbonyl compounds, see ref. [7c]. See also: K. Shibatomi, H. Yamamoto, Angew. Chem. Int. Ed. 2008, 47, 5796-5798.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5796-5798
    • Shibatomi, K.1    Yamamoto, H.2
  • 53
    • 70350203746 scopus 로고    scopus 로고
    • note
    • The three-component Mannich reaction between trifluoroacet-aldehyde ethyl hemiacetal, p-anisidine and aldehyde 2a only afforded products arising from the condensation of 2a with its derived imine.
  • 54
    • 70350183401 scopus 로고    scopus 로고
    • note
    • 2Cl group, without affecting to the establishment of the absolute configuration. This disorder has been omitted in Figure 2 for clarity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.