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Volumn 68, Issue 5, 2003, Pages 885-898

Diastereoselective addition of α-metalated sulfoxides to imines revisited: Mechanism, computational studies, and the effect of external chiral ligands

Author keywords

Asymmetric additions; Carbanions; Chiral sulfoxides; Diastereoselectivity; Imines; N ligands; Organolithium reagents; Quantum mechanical calculations

Indexed keywords

2 (ANILINO) 2 PHENYLETHYL 4 TOLYLSULFOXIDE; 2 TERT BUTYL 2 (2 METHOXYANILINO)ETHYL 4 TOLYLSULFOXIDE; LIGAND; SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0038044641     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20030885     Document Type: Article
Times cited : (7)

References (30)
  • 1
    • 0000739134 scopus 로고
    • For reviews, see: a) Solladié G.: Pure Appl. Chem. 1988, 60, 1699; b) Walker A. J.: Tetrahedron: Asymmetry 1992, 3, 961.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1699
    • Solladié, G.1
  • 2
    • 0026661770 scopus 로고
    • For reviews, see: a) Solladié G.: Pure Appl. Chem. 1988, 60, 1699; b) Walker A. J.: Tetrahedron: Asymmetry 1992, 3, 961.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 961
    • Walker, A.J.1
  • 15
    • 0037768595 scopus 로고    scopus 로고
    • Ph.D. Thesis. Technical University of Denmark, Lyngby
    • Pedersen B.: Ph.D. Thesis. Technical University of Denmark, Lyngby 2001.
    • (2001)
    • Pedersen, B.1
  • 16
    • 0000710827 scopus 로고
    • See, for example: Hubbard J. S., Harris T. M.: J. Org. Chem. 1981, 46, 2566. We are indebted to Prof. G. Solladié (Strasbourg) for pointing out the advantages of using demetalated silica gel.
    • (1981) J. Org. Chem. , vol.46 , pp. 2566
    • Hubbard, J.S.1    Harris, T.M.2
  • 17
    • 0038445431 scopus 로고    scopus 로고
    • http://www.schrodinger.com.
  • 20
    • 0027511699 scopus 로고
    • For the use of an external chiral ligand to enhance the diastereoselectivity of addition of an α-lithiated sulfoxide to a nitrone, see: Murahashi S.-I., Sun J., Tsuda T.: Tetrahedron Lett. 1993, 34, 2645.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2645
    • Murahashi, S.-I.1    Sun, J.2    Tsuda, T.3
  • 29
    • 0004150157 scopus 로고
    • Bruker AXS Analytical X-Ray Systems, Madison (WI)
    • Sheldrick G. M.: SHELXTL version 5.03. Bruker AXS Analytical X-Ray Systems, Madison (WI) 1994.
    • (1994) SHELXTL Version 5.03
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.