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Volumn 38, Issue 9, 1999, Pages 1219-1223

A stable and recoverable chiral Ru Lewis acid: Synthesis, asymmetric Diels-Alder catalysis and structure of the Lewis acid methacrolein complex

Author keywords

Asymmetric catalysis; Cycloadditions; Lewis acids; P ligands; Ruthenium

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MOLECULAR STABILITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033519296     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990503)38:9<1219::aid-anie1219>3.0.co;2-d     Document Type: Article
Times cited : (123)

References (44)
  • 18
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    • c) For a review of chiral recognition in transition metal Lewis acid π complexes of alkenes and carbonyl compounds, see J. A. Gladysz, B. J. Boone, Angew. Chem. 1997, 109, 566-602;
    • (1997) Angew. Chem. , vol.109 , pp. 566-602
    • Gladysz, J.A.1    Boone, B.J.2
  • 24
    • 85087244286 scopus 로고    scopus 로고
    • note
    • -1) acetone indicative of a σ-coordination mode of the ketone and a slow rate of exchange between free and coordinated acetone.
  • 27
    • 0000472173 scopus 로고
    • For conformational studies on Lewis acid methacrolcin complexes, see K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413, and references therein.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10412-10413
    • Ishihara, K.1    Gao, Q.2    Yamamoto, H.3
  • 28
    • 33745180480 scopus 로고    scopus 로고
    • note
    • -3. One of the two molecules shows an in-plane disorder of a phenyl group (angle between the two phenyl mean planes = 3.0(6)°). This disorder was resolved by refinement of two tilted positions (tilt angle of about 12°) with population parameters of 0.60 and 0.40, respectively, and restraints on bond lengths, bond angles, and torsional angles (40 restraints). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-112276. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 29
    • 33745126241 scopus 로고    scopus 로고
    • note
    • For the single literature precedent of a chiral Lewis acid-methacrolein complex, see ref. [4c].
  • 31
    • 0030913422 scopus 로고    scopus 로고
    • For a discussion of the importance of hydrogen bonds in Lewis acid coordinated aldehydes, see: E. J. Corey, D. Barnes-Seeman, T. W. Lee, Tetrahedron Lett. 1997, 38, 4351-4354.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4351-4354
    • Corey, E.J.1    Barnes-Seeman, D.2    Lee, T.W.3
  • 33
    • 85087244188 scopus 로고    scopus 로고
    • note
    • [2] An approach from all other than the top face is blocked by the chiral ligand.
  • 37
    • 85087247053 scopus 로고    scopus 로고
    • note
    • 6 was sluggish.
  • 39
    • 84985635661 scopus 로고
    • 4NBr to (S,S)-4d. For the use of a silver salt to carry out an analogous bromide abstraction, see: E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8966-8967
    • Corey, E.J.1    Loh, T.-P.2
  • 42
    • 33745136060 scopus 로고    scopus 로고
    • WebLab ViewerPro is a product of Molecular Simulation Inc., San Diego, Cal. USA
    • WebLab ViewerPro is a product of Molecular Simulation Inc., San Diego, Cal. USA; http://www.msi.com.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.