A stereoselective cyclization strategy for the preparation of γ-lactams and their use in the synthesis of α-Methyl-β-proline

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10925-10930

  Banerjee, Souvik ^a   Smith, Justin ^a   Smith, Jillian ^a   Faulkner, Caleb ^a   Masterson, Douglas S ^a  

^a University of Southern Mississippi   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; ELECTRONIC CONTROLS; LEAVING GROUPS; MALONIC ACID; MALONIC ESTER; MONOESTERS; STEREO-SELECTIVE; STEREOSELECTIVE CYCLIZATIONS;

AMIDES; AMINO ACIDS; CARBOXYLIC ACIDS; CONTROL; ENANTIOMERS;

CYCLIZATION;

ALPHA METHYLBETA PROLINE; BENZYL ALCOHOL; GAMMA LACTAM DERIVATIVE; MALONIC ACID; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ELECTRONICS; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

AMINO ACIDS; CYCLIZATION; ESTERS; LACTAMS; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 84870904928     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3015903     Document Type: Article

References (34)

1. Xue, Z.-Y.; Liu, L.-X.; Jiang, Y.; Yuan, W.-C.; Zhang, X.-M. Eur. J. Org. Chem. 2012, 251
2. Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594
3. Lebedev, A. Chem. Heterocycl. Compd. 2007, 43, 673
4. Dorbee, M.; Florent, J.-C.; Monneret, C.; Rager, M.-N.; Bertounesque, E. Synlett 2006, 591
5. Yokosaka, T.; Hamajima, A.; Nemoto, T.; Hamada, Y. Tetrahedron Lett. 2012, 53, 1245
6. Brenner, M.; Seebach, D. Helv. Chim. Acta 1999, 82, 2365
7. Khoukhi, M.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1986, 27, 1031
8. Park, J.-H.; Ha, J.-R.; Oh, S.-J.; Kim, J.-A.; Shin, D.-S.; Won, T.-J.; Lamb, Y.-F.; Ahn, a. C. Tetrahedron Lett. 2005, 46, 1755
9. Tan, D. Q.; Atherton, A. L.; Smith, A. J.; Soldi, C.; Hurley, K. A.; Fettinger, J. C.; Shaw, J. T. ACS Comb. Sci. 2012, 14, 218
10. Pohmakotr, M.; Yotapan, N.; Tuchinda, P.; Kuhakarn, C.; Reutrakul, V. J. Org. Chem. 2007, 72, 5016
11. Blanchet, J.; Pouliquen, M.; Lasne, M.-C.; Rouden, J. Tetrahedron Lett. 2007, 48, 5727
12. Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. J. Org. Chem. 1997, 62, 5215
13. Mohr, P.; Waespe-SÌarcÌević, N.; Tamm, C.; Gawronska, K.; Gawronski, J. K. Helv. Chim. Acta 1983, 66, 2501
14. Provencher, L.; Wynn, H.; Jones, J. B.; Krawczyk, A. R. Tetrahedron: Asymmetry 1993, 4, 2025
15. Tamm, C. Pure Appl. Chem. 1992, 64, 1187
16. Toone, E. J.; Jones, B. Tetrahedron: Asymmetry 1991, 2, 1041
17. Toone, E. J.; Werth, M. J.; Jones, J. B. J. Am. Chem. Soc. 1990, 112, 4946
18. Masterson, D. S.; Roy, K.; Rosado, D. A.; Fouche, M. J. Pept. Sci. 2008, 14, 1151
19. Smith, M. E.; Banerjee, S.; Shi, Y.; Schmidt, M.; Bornscheuer, U. T.; Masterson, D. S. ChemCatChem 2012, 4, 472
20. Kedrowski, B. L. J. Org. Chem. 2003, 68, 5403
21. Budny, J.; Stamm, H. Arch. Pharm. 1981, 314, 657
22. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
23. Castiglioni, E.; Di Fabio, R.; Gianotti, M.; Mesic, M.; Pavone, F.; Rast, S.; Stasi, P. GlaxoSmithKline, 2010.
24. Jahangir, A.; Soth, M.; Yang, H.; Lynch, S. M. Hoffmann-La Roche AG, 2011.
25. Thomas, J.; Liu, X.; Lin, E. Y.-S.; Zheng, G. Z.; Ma, B.; Caldwell, D.; Gucklan, K. M.; Kumaravel, G.; Taveras, A. G.; Inc., B. I. M. Biogen IDEC MA, Inc. US 2012/0190649 A1, 2012, p 110.
26. Angst, D.; Bollbuck, B.; Janser, P.; Quancard, J.; Stiefl, N. J.. Novartis. WO 2011/095452 A1, 2011, p 168.
27. Grafton, M.; Mansfield, A. C.; Fray, M. J. Tetrahedron Lett. 2010, 51, 1026
28. Andrews, R. C.; Brown, P. J.; Deaton, D. N.; Drewry, D. H.; Foley, M. A.; Garrison, D. T.; Marron, B. E.; Smalley, T. L.; Berman, J. M.; Noble, S. A.; Inc., G. Glaxo Inc. GB2295387 (A), 1996.
29. Castanedo, G.; Chan, B.; Goldstein, D. M.; Kondru, R. K.; Lucas, M. C.; Palmer, W. S.; Price, S.; Safina, B.; Savy, P. P. A.; Seward, E. M.; Sutherlin, D. P.; Sweeney, Z. k.; Genentech; Roche, H. L. Genentech, Hoffmann La Roche. WO2010138589 (A1), 2010.
30. Barraclough, P.; Dieterich, P.; Spray, C. A.; Young, D. W. Org. Biomol. Chem. 2006, 4, 1483
31. Campbell, E. L.; Zuhl, A. M.; Liu, C. M.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3009
32. Fokas, D.; Wang, Z. Synth. Commun. 2008, 38, 3816
33. Choi, Y.; Ishikawa, H.; Velcicky, J.; Elliott, G. I.; Miller, M. M.; Boger, D. L. Org. Lett. 2005, 7, 4539
34. Sasaki, H.; Carreira, E. M. Synthesis 2000, 2000, 135