메뉴 건너뛰기




Volumn 2, Issue 8, 1996, Pages 974-980

X-ray structural studies of highly enantioselective Mn(salen) epoxidation catalysts

Author keywords

Asymmetric epoxidations; Catalysis; Manganese complexes; Structure elucidation

Indexed keywords

ASYMMETRIC EPOXIDATION; CATALYST STRUCTURES; EPOXIDATION CATALYSTS; MANGANESE COMPLEXES; MN(SALEN) COMPLEXES; SOLUTION CONFORMATIONS; STRUCTURE ELUCIDATION; X-RAY STRUCTURAL STUDY;

EID: 0001761314     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020812     Document Type: Article
Times cited : (154)

References (50)
  • 2
    • 0001405437 scopus 로고
    • (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel. L. S. Hegedus), Pergamon. New York, Chapt. 11.1
    • b) E. N. Jacobsen in Comprehensive Organometullic Chemistry II (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel. L. S. Hegedus), Pergamon. New York, 1995, Vol. 12, Chapt. 11.1.
    • (1995) Comprehensive Organometullic Chemistry II , vol.12
    • Jacobsen, E.N.1
  • 20
    • 58249096669 scopus 로고
    • v catalysts as Lewis acids in asymmetric Diels-Alder reactions However, data obtained by us and others (ref. [8]) indicate that the catalysts employed in that study are actually (salen)Mn(IV) complexes that are not the active species in olefin epoxidation reactions
    • v catalysts as Lewis acids in asymmetric Diels-Alder reactions (Y. Yamashita, T. Katsuki, Synlett 1995, 829-830). However, data obtained by us and others (ref. [8]) indicate that the catalysts employed in that study are actually (salen)Mn(IV) complexes that are not the active species in olefin epoxidation reactions.
    • (1995) Synlett , pp. 829-830
    • Yamashita, Y.1    Katsuki, T.2
  • 23
    • 84890847141 scopus 로고    scopus 로고
    • note
    • III complexes have been Characterized structurally (refs. [10-11]), and the bond lengths in the salen ligands are very similar in all three systems.
  • 24
    • 0001520107 scopus 로고
    • While this manuscript was in preparation, the X-ray structure of a chiral (salen)Mn complex bearing unhindered substituents at the 5 and 5′ positions was reported
    • While this manuscript was in preparation, the X-ray structure of a chiral (salen)Mn complex bearing unhindered substituents at the 5 and 5′ positions was reported: M. T. Rispcns, A. Meetsma, B. L. Feringa, Recl. Trav. Chim. Pays-Bas 1994, 113, 413-415.
    • (1994) Recl. Trav. Chim. Pays-Bas , vol.113 , pp. 413-415
    • Rispcns, M.T.1    Meetsma, A.2    Feringa, B.L.3
  • 26
    • 37049118911 scopus 로고
    • For examples of structurally characterized achiral (salen)Mn complexes, see ref. [6] and
    • For examples of structurally characterized achiral (salen)Mn complexes, see ref. [6] and a) J. E. Davies, B. M. Gatehouse, J. Chem. Soc. Dalton Trans. 1973, 2523-2527.
    • (1973) J. Chem. Soc. Dalton Trans. , pp. 2523-2527
    • Davies, J.E.1    Gatehouse, B.M.2
  • 35
    • 84890845414 scopus 로고    scopus 로고
    • note
    • lntermolecular Mn ... Mn distances range from 5.78-12.54 Å and C ... C distances from 3.87-14.28 Å.
  • 36
    • 84890818579 scopus 로고    scopus 로고
    • note
    • The superimposed structures in Figure 2 were generated from the X-ray data using the molecular similarity, atom pick and rigid body fit options on QUANTA software (Molecular Simulations Inc.) and a Silicon Graphics/lndigo 2 system.
  • 39
    • 33845550903 scopus 로고
    • For the first presentation of the side-on approach model in the context of asymmetric epoxidation, see
    • For the first presentation of the side-on approach model in the context of asymmetric epoxidation, see: J. T. Groves, R. S. Myers, J. Am. Chem. Soc. 1983, 105, 5791-5796.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5791-5796
    • Groves, J.T.1    Myers, R.S.2
  • 40
    • 84989550908 scopus 로고
    • Katsuki has presented a related model involving approach of olefin over the diimine bridge along the ligand imine C=N bonds
    • Katsuki has presented a related model involving approach of olefin over the diimine bridge along the ligand imine C=N bonds: a) N. Hosoya, A. Hatayama, K. Yanai, H. Fujii, R. Irie, T. Katsuki, Synlett 1993, 641-645.
    • (1993) Synlett , pp. 641-645
    • Hosoya, N.1    Hatayama, A.2    Yanai, K.3    Fujii, H.4    Irie, R.5    Katsuki, T.6
  • 42
    • 0001519357 scopus 로고
    • Very recently, a mechanism has been presented for epoxidation with (salen)Mn complexes wherein oxygen-atom transfer proceeds via oxametallacyclic intermediates
    • Very recently, a mechanism has been presented for epoxidation with (salen)Mn complexes wherein oxygen-atom transfer proceeds via oxametallacyclic intermediates (P.-O. Norrby, C. Linde, B. Åkermark, J. Am. Chem. Soc. 1995,117, 11035-11036;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11035-11036
    • Norrby, P.-O.1    Linde, C.2    Åkermark, B.3
  • 43
    • 0030052488 scopus 로고    scopus 로고
    • However, we consider this mechanism to be untenable based on existing experimental data. We will present the basis for this evaluation in a separate paper
    • T. Hamada, T. Fukuda, H. Imanishi, T. Katsuki, Tetrahedron 1996, 52, 515-530). However, we consider this mechanism to be untenable based on existing experimental data. We will present the basis for this evaluation in a separate paper.
    • (1996) Tetrahedron , vol.52 , pp. 515-530
    • Hamada, T.1    Fukuda, T.2    Imanishi, H.3    Katsuki, T.4
  • 50
    • 84890827315 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-1220-13. Copies of the data can be obtained free of charge on application to The Director. CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: Int. code +(1223)336-033; email: teched@chemcrys.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.