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Volumn 10, Issue 3, 2004, Pages 699-707

New Dihydroxy Bis(Oxazoline) Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation: Experimental Investigations of the Origin of the Reversal of the Enantioselectivity

Author keywords

Allylic alkylation; Asymmetric catalysis; Enantioselectivity; N ligands; Palladium

Indexed keywords

ALKYLATION; MOLECULAR STRUCTURE; NEGATIVE IONS; PALLADIUM;

EID: 1242307880     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204649     Document Type: Article
Times cited : (55)

References (57)
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    • e) O. Reiser, Angew. Chem. 1993, 105, 576; Angew. Chem. Int. Ed. Engl. 1993, 32, 547;
    • (1993) Angew. Chem. , vol.105 , pp. 576
    • Reiser, O.1
  • 33
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    • e) O. Reiser, Angew. Chem. 1993, 105, 576; Angew. Chem. Int. Ed. Engl. 1993, 32, 547;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 547
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    • (Eds.: E. N. Jacobson, A. Pfaltz, H. Yamamoto), Springer, Berlin, Chapter 24
    • g) A. Pfaltz, M. Lautens, in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobson, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Chapter 24.
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 2 , vol.2
    • Pfaltz, A.1    Lautens, M.2
  • 37
    • 84987472013 scopus 로고
    • For previous use of chiral bis(oxazoline) ligands in the palladium-catalyzed asymmetric allylic alkylation, see: a) D. Muller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232;
    • (1991) Helv. Chim. Acta , vol.74 , pp. 232
    • Muller, D.1    Umbricht, G.2    Weber, B.3    Pfaltz, A.4
  • 44
  • 45
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    • d) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614; Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 566
  • 46
    • 85039562381 scopus 로고    scopus 로고
    • note
    • No solvent effect on this shift in the enantioselectivity was observed.
  • 49
    • 85039584155 scopus 로고    scopus 로고
    • note
    • The verification of other bases such as nBuLi, HK, and tBuMgCl did not show any effect on the direction of chiral induction, but affected the level of enantioselectivity. For example, in the presence of nBuLi as a base BO 1a afforded the R product in 53% ee and 1b led to the S product in 28% ee.
  • 53
    • 85039562482 scopus 로고    scopus 로고
    • note
    • The silylation of the dihydroxy BO was ruled out because it is unlikely that this reaction could occurs under the BSA/KOAc procedure. Efforts were made for the preparation of this disylilated BO ligand. This disilylated BO was found to be very instable under the BSA/KOAc conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.