메뉴 건너뛰기




Volumn 43, Issue 3, 2004, Pages 317-320

Efficient Synthesis of Chiral α- and β-Hydroxy Amides: Application to the Synthesis of (R)-Fluoxetine

Author keywords

Asymmetric synthesis; Epoxides; Regioselectivity; Synthetic methods

Indexed keywords

HYDROXYLATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 0347131086     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352431     Document Type: Article
Times cited : (91)

References (36)
  • 1
    • 0037556625 scopus 로고
    • (Ed.: Atta-ur-Rahman), Elsevier
    • For reviews, see: a) Studies in Natural Products Chemistry, Vol. 2 (Ed.: Atta-ur-Rahman), Elsevier, 1988, p. 680;
    • (1988) Studies in Natural Products Chemistry , vol.2 , pp. 680
  • 4
    • 84985530075 scopus 로고
    • c) S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1-30
  • 6
    • 0037122049 scopus 로고    scopus 로고
    • a) S. N. Goodman, E. N. Jacobsen, Angew. Chem. 2002, 114, 4897-4899; Angew. Chem. Int. Ed. 2002, 41, 4703-4705;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4703-4705
  • 10
    • 0038007833 scopus 로고    scopus 로고
    • Recently, the transformation of β-aryl substituted α,β-epoxy amides into α-hydroxy amides (path A) using samarium(n) iodide was reported, see: J. M. Concellón, E. Bardales, C. Gómez, Tetrahedron Lett. 2003, 44, 5323-5326.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5323-5326
    • Concellón, J.M.1    Bardales, E.2    Gómez, C.3
  • 18
    • 0347613737 scopus 로고    scopus 로고
    • note
    • Based on the HPLC analysis, there was no racemization in the epoxide-opening process; see the Supporting Information for details.
  • 24
    • 0038732511 scopus 로고    scopus 로고
    • The role of counterions in the regioselective opening of 2,3-epoxy alcohol was studied theoretically, see: I. Infante, C. Bonini, F. Leij, G. Righi, J. Org. Chem. 2003, 68, 3773-3780. These results also support our hypothesis.
    • (2003) J. Org. Chem. , vol.68 , pp. 3773-3780
    • Infante, I.1    Bonini, C.2    Leij, F.3    Righi, G.4
  • 25
    • 0348243530 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for details.
  • 26
    • 0348243531 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 11a was determined to be 2R, 3S. See the Supporting Information for details.
  • 36
    • 0342601552 scopus 로고    scopus 로고
    • After the epoxide-opening reaction, [15]crown-5 was recovered in 87% yield. See the Supporting Information. Alternatively, immobilized crown ethers can be applied to this reaction. For an example of the immobilization of crown ethers, see: A. Favre-Réguillon, N. Dumont, B. Dunjic, M. Lemaire, Tetrahedron Lett. 1997, 38, 1343-1360.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1343-1360
    • Favre-Réguillon, A.1    Dumont, N.2    Dunjic, B.3    Lemaire, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.