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Volumn 43, Issue 1, 2004, Pages 84-87

Kinetic Resolution of Epoxides by a C-C Bond-Forming Reaction: Highly Enantioselective Addition of Indoles to cis, trans, and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes

Author keywords

Aromatic epoxides; Asymmetric catalysis; Indoles; Kinetic resolution; N,O ligands

Indexed keywords

ENANTIOMERIC RESOLUTION;

EID: 33745830746     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352073     Document Type: Article
Times cited : (106)

References (39)
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    • K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
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    • Sharpless, K.B.1
  • 3
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    • K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2024-2032
  • 4
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    • K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
    • (1995) Coord. Chem. Rev. , vol.140 , pp. 189-214
    • Katsuki, T.1
  • 11
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    • e) R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753; Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3604-3607
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    • g) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
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    • Ready, J.M.1    Jacobsen, E.N.2
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    • g) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1374-1377
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    • Kinetic resolution of 2,2-disubstituted epoxides catalyzed by [Cr(salen)]: H. Lebel, E. N. Jacobsen, Tetrahedron Lett. 1999, 40, 7303-7306.
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    • Springer, Berlin
    • Kinetic resolution of 1,2-disubstituted epoxides with enzymes: K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 2000, pp. 135-136.
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    • Kinetic resolution of epoxides via C-heteroatom bond-forming reactions: a) S. E. Schaus, E. N. Jacobsen, Tetrahedron Lett. 1996, 37, 7937-7940;
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    • Important examples of ARO reactions of meso epoxides with carbon nucleophiles: a) M. B. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
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    • note
    • Other indoles (indole; 1-methyl-, 5-methoxy-, 5-bromo-, 5-benzyloxy-, and 5-nitroindole) were less reactive than 2-methyindole.
  • 33
    • 0037138704 scopus 로고    scopus 로고
    • Interestingly, the absolute configuration of isolated 1a was the opposite of that in other kinetic resolutions carried out with [Cr(salen)] and [Co(salen)] complexes, and this indicates that a different mechanism is probably operative in this case. For [Co(salen)]-catalyzed kinetic resolution, see S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315. For kinetic resolution employing [Cr(salen)], see ref. [7e].
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1307-1315
    • Schaus, S.E.1    Brandes, B.D.2    Larrow, J.F.3    Tokunaga, M.4    Hansen, K.B.5    Gould, A.E.6    Furrow, M.E.7    Jacobsen, E.N.8
  • 35
    • 0346398726 scopus 로고    scopus 로고
    • note
    • Absolute configurations of products 2a, 2f, and 2i were established by HPLC analysis by comparing the retention times with those of authentic samples; for all other products the absolute configuration was assigned by analogy.
  • 36
    • 0347659672 scopus 로고    scopus 로고
    • note
    • The lower limit of the selectivity factor s for the epoxides was estimated by using the equation s=ln[1-c(1+ee)]/ ln[1-c(1-c(1-ee)] in the reaction with 2-methylindole (ee is the percentage enantiomeric excess of the ring-opened products; yields of ring-opened products were used for conversion c.
  • 37
    • 0346398721 scopus 로고    scopus 로고
    • note
    • The amount of 2-methylindole was adjusted to obtain the maximum yield possible with the highest enantiomeric excess for the unconverted epoxides. As we use 0.6-0.7 equiv of 2-methylindole, the maximum theoretical yield is 30-40%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.