High enantioselection in the rearrangement of allylic imidates with ferrocenyl oxazoline catalysts

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2933-2934

  Donde, Yariv ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; FERROCENE DERIVATIVE; OXAZOLINE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033620464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983263q     Document Type: Article

References (21)

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6. For other examples of the use of oxidative addition for the synthesis of palladacycles, see: (a) Denmark, S. E.; Stavenger, R. A.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375. (b) Mateo, C.; Cardenas, D. J.; Fernandez-Rivas, C.; Echavarren, A. M. Chem.-Eur. J. 1996, 2, 1596.
7. For other examples of the use of oxidative addition for the synthesis of palladacycles, see: (a) Denmark, S. E.; Stavenger, R. A.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375. (b) Mateo, C.; Cardenas, D. J.; Fernandez-Rivas, C.; Echavarren, A. M. Chem.-Eur. J. 1996, 2, 1596.
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9. These conditions are adapted from the following: Rebiere, F.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1990, 31, 3121.
10. Experimental details for preparing these catalysts and their characterization data are provided in the Supporting Information.
11. For a review of palladacycle synthesis, see: Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 9, pp 242-248.
12. The authors have deposited coordinates for these compounds with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
13. 2) δ 5.14 (d, J = 1.9 Hz 1 H), 4.76 (dd, J = 8.9, 2.9, 1 H), 4.60 (app t, J = 8.9 Hz, 1 H), 4.36 (s, 5 H), 4.24 (br m, 1 H), 3.69 (dd, J = 8.5, 2.9 Hz, 1 H), 0.95 (s, 9 H), 0.22 (s, 9 H).
14. Catalysts 10b and 11b were markedly less stable than catalysts 7b-9b as signaled by the deposit of a black solid during the catalytic reactions reported in Table 1, entries 7-10.
15. 2.
16. 2. Attempted formation of a triflate catalyst by treatment of 7a with AgOTf resulted in apparent catalyst decomposition. Toluene was also a suitable reaction solvent, although reaction times were somewhat longer.
17. 3).
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