Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source

Journal of the American Chemical Society

Volumn 124, Issue 50, 2002, Pages 14850-14851

  Bolm, Carsten ^a   Rudolph, Jens ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BORONIC ACID DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHIRALITY; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; BENZYL ALCOHOLS; BORONIC ACIDS; CATALYSIS; METHANOL;

EID: 0037132590     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028518l     Document Type: Article

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36. For B-to-Zn exchange reactions involving alkenylboranes, see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. (d) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (e) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414. (f) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
37. For B-to-Zn exchange reactions involving alkenylboranes, see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. (d) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (e) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414. (f) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
38. For B-to-Zn exchange reactions involving alkenylboranes, see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. (d) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (e) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414. (f) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
39. For B-to-Zn exchange reactions involving alkenylboranes, see: (a) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593. (d) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229. (e) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414. (f) Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
40. 5 the diarylmethanols are obtained in analytically pure form after column chromatography (silica gel, pentane:diethyl ether = 85:15).
41. Bolm, C.; Hermanns, N.; Rudolph, J., manuscript in preparation.