Chiral 2,2′-bipyridine-type N-monoxides as organocatalysts in the enantioselective allylation of aldehydes with allyltrichlorosilane

Organic Letters

Volumn 4, Issue 6, 2002, Pages 1047-1049

  Malkov, Andrei V ^a   Orsini, Monica ^a   Pernazza, Daniele ^a   Muir, Ken W ^a   Langer, Vratislav ^b   Meghani, Premji ^c   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^c ASTRAZENECA   (United Kingdom)

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ARTICLE;

EID: 0001056484     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025654m     Document Type: Article

References (49)

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30. (a) Malkov, A. V.; Bella, M.; Langer, V. Kočovský, P. Org. Lett. 2000, 2, 3047.
31. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russel, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673.
32. (c) A new, 3-step synthesis of (+)-5 from the commercially available (+)-nopinone is now being optimized: Malkov, A. V.; Teplý, F.; Herrmann, P.; Kočovský, P. Unpublished results.
33. For an overview on the synthesis of chiral bipyridines, see: (a) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 303.
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37. For analogous (phosphinoaryl)pyridines, see: Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045.
38. (b) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989.
39. In contrast to (S)-4, the rotation barriers in (-)-7 and (+)-8 are too low to allow the separation of atropoisomers.
40. 2 group rather than its electronic effect (compare entries 9 and 10).
41. 6,8,13
42. Hexacoordinated complexes of bidentate pyridine-derived N,N-monoxides with metals, such as Cu(II) and Co(II), have been reported: (a) Anderson, R. J.; Hagback, P. H.; Steel, P. J. Inorg. Chim. Acta 1999, 284, 273.
43. (b) Vrbová, M.; Baran, P.; Boča, R.; Fuess, H.; Svoboda, I.; Linert, W.; Schubert, U.; Wiede, P. Polyhedron 2000, 19, 2195.
44. 13 where the stereo-electronic effects were not considered. Note that while 4 and 7 allow the formation of a seven-membered chelate, 8 should operate via a six-membered ring.
45. In solution, the two atropoisomers slowly interconvert at room temperature, eventually reaching the thermodynamic equilibrium within about a week. In the solid state, (+)-9 appears to be reasonably stable when stored in a freezer.
46. F = 0.0534. Two molecules are present in the cell, differing from each other, e.g., in the dihedral angle N(O)-C(2)-C(2′)-N (100.6° and 102.6°, respectively).
47. F = 1.021.
48. 4, catalyzed by (+)-8, afforded the corresponding chlorohydrin of 85% ee, which is the highest enantioselectivity reported to date. For other examples of this reaction and a recent discussion, see: (a) Denmark, S. E.; Wunn, T.; Jellerichs, B. G. Angew. Chem., Int. Ed. 2001, 40, 2255 and references cited therein. For a withdrawal of earlier claims, see: (b) Buono, G. Angew. Chem., Int. Ed. 2001, 40, 4536.
49. 4, catalyzed by (+)-8, afforded the corresponding chlorohydrin of 85% ee, which is the highest enantioselectivity reported to date. For other examples of this reaction and a recent discussion, see: (a) Denmark, S. E.; Wunn, T.; Jellerichs, B. G. Angew. Chem., Int. Ed. 2001, 40, 2255 and references cited therein. For a withdrawal of earlier claims, see: (b) Buono, G. Angew. Chem., Int. Ed. 2001, 40, 4536.