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
References
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, and Hewitt BD. inventors; US 6,211,386.
; Chem. Abstr. 2000 , 133 , 252309
10a Burk MJ, Goel OP, Hoekstra MS, Mich TF, Mulhern TA, and Ramsden 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
14 Lennon, I. C. in Proceedings
of the BACS 2001 Symposium , British Association for Chemical
Specialities, Lancaster, UK, 2001.
15
Burk MJ.
Acc.
Chem. Res.
2000,
33:
363
16 Pilkington, C. J.; Zanotti-Gerosa,
A. Org. Lett. 2003 , 5, 1273.
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