Enantioselective synthesis of (R)-tolterodine using lithiation/borylation- protodeboronation methodology

Canadian Journal of Chemistry

Volumn 90, Issue 11, 2012, Pages 965-974

  Roesner, Stefan ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Asymmetric synthesis; Boronic esters; gem diarylalkyl; Lithiation borylation reaction; Tolterodine

Indexed keywords

ASYMMETRIC SYNTHESIS; BORONIC ESTERS; EFFICIENT SYNTHESIS; ELECTRON-RICH; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; HIGH YIELD; LITHIATION; MAGNESIUM BROMIDE; TOLTERODINE;

BROMINE COMPOUNDS; ELECTRONS; ESTERIFICATION; ESTERS; MAGNESIUM; METHANOL;

ENANTIOSELECTIVITY;

EID: 84870933816     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v2012-069     Document Type: Article

References (38)

1. a Prat L. Mojovic L. Levacher V. Dupas G. Quéguiner G. Bourguignon J. Tetrahedron Asymmetry 1998, 9 (14), 2509. 10.1016/S0957-4166(98)00228-6
2. b Selim K. B. Matsumoto Y. Yamada K. Tomioka K. Angew. Chem. Int. Ed. 2009, 48 (46), 8733. and references therein. 10.1002/anie.200904676
3. a Nilvebrant L. Andersson K.-E. Gillberg P.-G. Stahl M. Sparf B. Eur. J. Pharmacol. 1997, 327 (2-3), 195. 10.1016/S0014-2999(97)89661-6
4. b Hills C. J. Winter S. A. Balfour J. A. Drugs 1998, 55 (6), 813. 10.2165/00003495-199855060-00008
5. Pfizer Annual Report to Shareholders, 2008.
6. Jönsson, N. A.; Sparf, B. A.; Mikiver, L.; Moses, P.; Nilvebrant, L.; Glas, G. EP 0325571, A1, 1989.
7. Andersson P. G. Schink H. E. Österlund K. J. Org. Chem. 1998, 63 (22), 8067. 10.1021/jo981259r
8. Hedberg C. Andersson P. G. Adv. Synth. Catal. 2005, 347 (5), 662. 10.1002/adsc.200404234
9. a Ulgheri F. Marchetti M. Piccolo O. J. Org. Chem. 2007, 72 (16), 6056. 10.1021/jo0705667
10. b Jagdale A. R. Sudalai A. Tetrahedron Lett. 2008, 49 (23), 3790. 10.1016/j.tetlet.2008.04.007
11. c Gallagher B. D. Taft B. R. Lipshutz B. H. Org. Lett. 2009, 11 (23), 5374. 10.1021/ol9020404
12. d Yoo K. Kim H. Yun J. J. Org. Chem. 2009, 74 (11), 4232. 10.1021/jo900530s
13. e Wang X. Guram A. Caille S. Hu J. Preston J. P. Ronk M. Walker S. Org. Lett. 2011, 13 (7), 1881. 10.1021/ol200422p
14. Botteghi C. Corrias T. Marchetti M. Paganelli S. Piccolo O. Org. Process Res. Dev. 2002, 6 (4), 379. 10.1021/op020014k
15. a Chen G. Tokunaga N. Hayashi T. Org. Lett. 2005, 7 (11), 2285. 10.1021/ol0507367
16. b Sörgel S. Tokunaga N. Sasaki K. Okamoto K. Hayashi T. Org. Lett. 2008, 10 (4), 589. 10.1021/ol702879u
17. c Kobayashi K. Nishikata T. Yamamoto Y. Miyaura N. Bull. Chem. Soc. Jpn. 2008, 81 (8), 1019. 10.1246/bcsj.81.1019
18. a Stymiest J. L. Bagutski V. French R. M. Aggarwal V. K. Nature 2008, 456 (7223), 778. 10.1038/nature07592
19. b Bagutski V. French R. M. Aggarwal V. K. Angew. Chem. Int. Ed. 2010, 49 (30), 5142. 10.1002/anie.201001371
20. c. These reactions are based on the seminal studies by Hoppe on the lithiation and trapping of secondary benzylic carbamates. See Hoppe D. Carstens A. Krämer T. Angew. Chem. Int. Ed. Engl. 1990, 29 (12), 1424. 10.1002/anie.199014241
21. d Carstens A. Hoppe D. Tetrahedron 1994, 50 (20), 6097. 10.1016/S0040-4020(01)90461-2
22. a Nave S. Sonawane R. P. Elford T. G. Aggarwal V. K. J. Am. Chem. Soc. 2010, 132 (48), 17096. 10.1021/ja1084207
23. b Roesner S. Casatejada J. M. Elford T. G. Sonawane R. P. Aggarwal V. K. Org. Lett. 2011, 13 (21), 5740. 10.1021/ol202251p
24. c Elford T. G. Nave S. Sonawane R. P. Aggarwal V. K. J. Am. Chem. Soc. 2011, 133 (42), 16798. 10.1021/ja207869f
25. d Aggarwal V. K. Ball L. T. Carobene S. Connelly R. L. Hesse M. J. Partridge B. M. Roth P. Thomas S. P. Webster M. P. Chem. Commun. 2012, 48, 9230. 10.1039/C2CC32176A
26. a Koe B. K. Weissman A. Welch W. M. Browne R. G. J. Pharmacol. Exp. Ther. 1983, 226, 686
27. b Welch W. M. Kraska A. R. Sarges R. Koe B. K. J. Med. Chem. 1984, 27 (11), 1508. 10.1021/jm00377a021
28. Maggon K. Drug Discov. Today 2005, 10 (11), 739. 10.1016/S1359-6446(05) 03468-9
29. a Bogeso K. P. Christensen A. V. Hyttel J. Liljefors T. J. Med. Chem. 1985, 28 (12), 1817. 10.1021/jm00150a012
30. b Hyttel J. Larsen J. J. J. Neurochem. 1985, 44 (5), 1615. 10.1111/j.1471-4159.1985.tb08803.x
31. Negus S. S. Brandt M. R. Mello N. K. J. Pharmacol. Exp. Ther. 1999, 291, 60.
32. Jadhav P. K. Bhat K. S. Perumal P. T. Brown H. C. J. Org. Chem. 1986, 51 (4), 432. 10.1021/jo00354a003
33. Yu W. Mei Y. Kang Y. Hua Z. Jin Z. Org. Lett. 2004, 6 (19), 3217. 10.1021/ol0400342
34. Pangborn A. B. Giardello M. A. Grubbs R. H. Rosen R. K. Timmers F. J. Organometallics 1996, 15 (5), 1518. 10.1021/om9503712
35. Roush W. R. Walts A. E. Hoong L. K. J. Am. Chem. Soc. 1985, 107 (26), 8186. 10.1021/ja00312a062
36. Kahnberg P. Lager E. Rosenberg C. Schougaard J. Camet L. Sterner O. Nielsen E. O. Nielsen M. Liljefors T. J. Med. Chem. 2002, 45 (19), 4188. 10.1021/jm020839k
37. Tokunaga N. Hayashi T. Tetrahedron Asymmetry 2006, 17 (4), 607. 10.1016/j.tetasy.2006.01.036
38. Paras N. A. Simmons B. MacMillan D. W. C. Tetrahedron 2009, 65 (16), 3232. 10.1016/j.tet.2008.12.054