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DOI: 10.1055/s-2003-40871
The Application of Asymmetric Hydrogenation for the Manufacture of Pharmaceutical Intermediates: The Need for Catalyst Diversity
Publication History
Publication Date:
25 July 2003 (online)
Abstract
Asymmetric hydrogenation is becoming an increasingly prevalent technology for the manufacture of complex pharmaceutical intermediates. Drawing from Chirotech’s experience over the past eight years, this article emphasises the need for a diverse catalyst collection in providing practical solutions for a wide range of target compounds.
Key words
asymmetric hydrogenation - diversity - DuPhos - ligands - catalyst collection
- 1
De Camp WH. Chirality 1989, 1: 2 -
2a
Comprehensive Asymmetric Catalysis
Vols.
I-III:
Jacobsen EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999. -
2b
Asymmetric
Catalysis in Organic Synthesis
Noyori R. John Wiley & Sons; New York: 1993. - For transcripts of their Nobel Lectures see:
-
3a
Knowles WS. Angew. Chem. Int. Ed. 2002, 41: 1998 -
3b
Noyori R. Angew. Chem. Int. Ed. 2002, 41: 2008 -
3c
Sharpless BK. Angew. Chem. Int. Ed. 2002, 41: 2024 - 4
Knowles WS. Acc. Chem. Res. 1983, 16: 106 - 5
Blaser HU.Spindler F.Studer M. Appl. Catal., A 2001, 221: 119 -
6a
Burk MJ. J. Am. Chem. Soc. 1991, 113: 8518 -
6b
Burk MJ.Feaster JE.Nugent WA.Harlow RL. J. Am. Chem. Soc. 1993, 115: 10125 -
6c
Burk MJ.Gross MF.Martinez JP. J. Am. Chem. Soc. 1995, 117: 9375 -
6d
Burk MJ.Wang YM.Lee JR. J. Am. Chem. Soc. 1996, 118: 5142 -
6e
Burk MJ.Gross MF.Harper TGP.Kalberg CS.Lee JR.Martinez JP. Pure Appl. Chem. 1996, 68: 37 -
6f
Debenham SD.Debenham JS.Burk MJ.Toone EJ. J. Am. Chem. Soc. 1997, 117: 9897 -
6g
Burk MJ.Allen JG.Kiesman WF. J. Am. Chem. Soc. 1998, 120: 657 -
6h
Burk MJ.Kalberg CS.Pizzano A. J. Am. Chem. Soc. 1998, 120: 4345 -
6i
Burk MJ.Casy G.Johnson NB. J. Org. Chem. 1998, 63: 6084 - 7
Burk MJ.Bienewald F. Unnatural α-Amino Acids via Asymmetric Hydrogenation of Enamides, In Transition Metals for Organic Synthesis and Fine Chemicals Vol. 2: Wiley-VCH; Weinheim, Germany: 1998. p.13 - 8
Burk MJ.Bienewald F.Challenger S.Derrick A.Ramsden JA. J. Org. Chem. 1999, 64: 3290 - 9
Burk MJ,Johnson NM, andHewitt BD. inventors; US 6,211,386. ; Chem. Abstr. 2000, 133, 252309 -
10a
Burk MJ,Goel OP,Hoekstra MS,Mich TF,Mulhern TA, andRamsden JA. inventors; WO 01/55090 A1. ; Chem. Abstr. 2001, 135, 122750 -
10b
Burk, M. J.; de Koning, P. D.; Grote, T. M.; Hoekstra, M. S.; Hoge, G.; Jennings, R. A.; Kissel, W. S.; Le, T. V.; Lennon, I. C.; Mulhern, T. A.; Ramsden, J. A.; Wade, R. A. J. Org. Chem. 2003, 68, in press.
- 11
Burk MJ.Bienewald F.Harris M.Zanotti-Gerosa A. Angew. Chem. Int. Ed. 1998, 37: 1931 - 12
Berens U.Burk MJ.Gerlach A.Hems W. Angew. Chem. Int. Ed. 2000, 39: 1981 - 13
Cobley C.Lennon IC.Praquin P.Zanotti-Gerosa A.Appel RB.Goralski CT.Sutterer AC. Process Res. Dev. 2003, 7: 407 - 15
Burk MJ. Acc. Chem. Res. 2000, 33: 363 - 17
Boulton LT.Lennon IC.McCague R. Org. Biomol. Chem. 2003, 1: 1094 - 18
Noyori R.Ohkuma T. Angew. Chem. Int. Ed. 2001, 40: 40 - 19
Burk MJ.Hems W.Herzberg D.Malan C.Zanotti-Gerosa A. Org. Lett. 2000, 2: 4173 - 20
Chaplin D.Harrison P.Henschke JP.Lennon IC.Meek G.Moran P.Pilkington CJ.Ramsden JA.Watkins S.Zanotti-Gerosa A. Org. Process Res. Dev. 2003, 7: 89 - 21
Henschke JP.Burk MJ.Malan CG.Herzberg D.Peterson JA.Wildsmith AJ.Cobley CJ.Casy G. Adv. Synth. Catal. 2003, 345: 300 - 22 Henschke, J. P.; Zanotti-Gerosa,
A.; Moran, P.; Harrison, P.; Mullen, B.; Casy, G.; Lennon, I. C. Tetrahedron Lett. 2003, 44, 4379
- 23
Cobley CJ.Henschke JP. Adv. Synth. Catal. 2003, 345: 195 - 24
Yue T.-Y.Nugent WA. J. Am. Chem. Soc. 2002, 124: 13692 - 25
Blaser HU. Chem. Commun. 2003, 293
References
Lennon, I. C. in Proceedings of the BACS 2001 Symposium, British Association for Chemical Specialities, Lancaster, UK, 2001.
16Pilkington, C. J.; Zanotti-Gerosa, A. Org. Lett. 2003, 5, 1273.