Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(5): 840-842
DOI: 10.1055/s-2004-834887
DOI: 10.1055/s-2004-834887
PSP
© Georg Thieme Verlag Stuttgart · New York
Boronic Acids as Versatile Aryl Sources for the Highly Enantioselective Synthesis of Chiral Diarylmethanols on Multigram Scale
Further Information
Received
16 July 2004
Publication Date:
21 October 2004 (online)
Publication History
Publication Date:
21 October 2004 (online)
Abstract
Chiral diarylmethanols have been synthesized on gram scale in high yields with excellent enantioselectivities using a catalyst with a ferrocenyl oxazoline-based N,O-ligand and mixtures of diethylzinc and arylboronic acid as an aryl source.
Key words
diarylmethanols - zinc organyls - catalysis - arylboronic acids
- 1 Pharma Overview:
Class S. Chem. Eng. News 2002, 80(48): 44 - 2 For a recent overview on Enantioselective Catalysis, see:
Chemical Reviews
Vol. 103:
Bolm C.Gladysz J. American Chemical Society; Washington D. C.: 2003. -
3a
Meguro K.Aizawa M.Sohda T.Kawamatsu Y.Nagaoka A. Chem. Pharm. Bull. 1985, 33: 3787 -
3b
Toda F.Tanaka K.Koshiro K. Tetrahedron: Asymmetry 1991, 2: 873 -
3c
Stanev S.Rakovska R.Berova N.Snatzke G. Tetrahedron: Asymmetry 1995, 6: 183 -
3d
Botta M.Summa V.Corelli F.Pietro GD.Lombardi P. Tetrahedron: Asymmetry 1996, 7: 1263 - 4
Bolshan Y.Chen C.-y.Chilenski JR.Gosselin F.Mathre DJ.O’Shea PD.Roy A.Tillyer RD. Org. Lett. 2004, 6: 111 ; and references cited therein -
5a
Ohkuma T.Koizumi M.Ikehira H.Yokozawa T.Noyori R. Org. Lett. 2000, 2: 659 -
5b
Corey EJ.Helal CJ. Tetrahedron Lett. 1995, 36: 9153 -
5c
Corey EJ.Helal CJ. Tetrahedron Lett. 1996, 37: 4837 -
5d
Corey EJ.Helal CJ. Tetrahedron Lett. 1996, 37: 5675 -
5e General Review:
Corey EJ.Helal CJ. Angew. Chem. Int. Ed. 1998, 37: 1986 ; Angew. Chem. 1998, 110, 2092 -
5f General Review:
Noyori R.Ohkuma T. Angew. Chem. Int. Ed. 2001, 40: 40 ; Angew. Chem. 2001, 113, 40 -
5g See also:
Noyori R. Angew. Chem. Int. Ed. 2002, 41: 2008 ; Angew. Chem. 2002, 114, 2108 - 6 For enantioselective hydrogenations of aromatic and heteroaromatic ketones, see:
Chen C.-y.Reamer RA.Chilenski JR.McWilliams CJ. Org. Lett. 2003, 5: 5039 -
7a
Dosa PI.Ruble JC.Fu GC. J. Org. Chem. 1997, 62: 444 -
7b
Huang W.-S.Hu Q.-S.Pu L. J. Org. Chem. 1999, 64: 7940 -
7c
Huang W.-S.Pu L. Tetrahedron Lett. 2000, 41: 145 -
7d
Zhao G.Li X.-G.Wang X.-R. Tetrahedron: Asymmetry 2001, 12: 399 -
7e
Ko D.-H.Kim KH.Ha D.-C. Org. Lett. 2002, 21: 3759 -
7f
Fontes M.Verdaguer X.Solà L.Pericàs MA.Riera A. J. Org. Chem. 2004, 69: 2532 -
8a
Bolm C.Muñiz K. Chem. Commun. 1999, 1295 -
8b
Bolm C.Hermanns N.Hildebrand JP.Muñiz K. Angew. Chem. Int. Ed. 2000, 39: 3465 ; Angew. Chem. 2000, 112, 3607 -
8c
Bolm C.Kesselgruber M.Hermanns N.Hildebrand JP. Angew. Chem. Int. Ed. 2001, 40: 1488 ; Angew. Chem. 2001, 113, 1536 -
8d
Bolm C.Kesselgruber M.Grenz A.Hermanns N.Hildebrand JP. New J. Chem. 2001, 25: 13 -
8e
Bolm C.Hermanns N.Kesselgruber M.Hildebrand JP. J. Organomet. Chem. 2001, 624: 157 -
8f
Bolm C.Hermanns N.Claßen A.Muñiz K. Bioorg. Med. Chem. Lett. 2002, 12: 1795 -
8g For a review on asymmetric arylation reactions, see:
Bolm C.Hildebrand JP.Muñiz K.Hermanns N. Angew. Chem. Int. Ed. 2001, 40: 3284 ; Angew. Chem. 2001, 113, 3382 - 9
Bolm C.Rudolph J. J. Am. Chem. Soc. 2002, 124: 14850 - 10
Rudolph J.Hermanns N.Bolm C. J. Org. Chem. 2004, 69: 3997 - 11
Rudolph J.Schmidt F.Bolm C. Adv. Synth. Catal. 2004, 346: 867 - 12
Lee J.-S.Velarde-Ortiz R.Guijarro A.Wurst JR.Rieke RD. J. Org. Chem. 2000, 65: 5428 - 13
Nakamura S.Oda M.Yasuda H.Toru T. Tetrahedron 2001, 57: 8469 - 14
Brown E.Leze A.Touet J. Tetrahedron: Asymmetry 1992, 3: 841