Highly diastereo- and enantioselective intramolecular amidation of saturated C-H bonds catalyzed by ruthenium porphyrins

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3465-3468

  Liang, Jiang Lin ^a   Yuan, Shi Xue ^a   Huang, Jie Sheng ^a   Yu, Wing Yiu ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Asymmetric catalysis; Cyclization; Porphyrinoids; Ruthenium; Sulfamidates

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; ESTERS;

DIASTEREOSELECTIVITY;

RUTHENIUM COMPOUNDS;

PORPHYRIN; RUTHENIUM; SULFATE;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037119816     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3465::AID-ANIE3465>3.0.CO;2-D     Document Type: Article

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34. The structures of racemic 4, 13, and 14 have been determined by X-ray crystallography. CCDC-184691 (4), CCDC-184693 (13), and CCDC-184694 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam. ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
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36. For examples of other metal-catalyzed asymmetric reactions that show strong solvent effects on enantioselectivity, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) M. Ogasawara, H. Ikeda, T. Nagano, T. Hayashi, J. Am. Chem. Soc. 2001, 123, 2089.
37. [12] The single crystal used for the structure determination was obtained from an optically active sample of 4 with 82% ee. The small absolute structure parameter of 0.15(12) derived from the structure determination confirms the chirality of the crystal.
38. 2 (P. Dauban, R. H. Dodd, J. Org. Chem. 1999, 64, 5304).
39. 3, 400 MHz) of 19: δ=7.89 (d,J=7.8 Hz, 2H), 7.54 (t. J=7.4 Hz, 1H), 7.33 (t, J=7.7 Hz, 2 H), 7.16 (m, 4H), 5.19 (m, 1H), 3.06 (m, 4H). The rather high instability of 19 renders it difficult to characterize this compound fully.
40. 2, under otherwise the same conditions, led to a decrease in the ee value of 11 from 46 to 39%. Notice that some other metal-catalyzed asymmetric reactions also show significant dependence of enantioselectivity on catalyst loading (see for example: H. M. L. Davies, T. Hansen, M. R. Churchill, J. Am. Chem. Soc. 2000, 122, 3063).