Enantioselective conjugate addition nitro-mannich reactions: Solvent controlled synthesis of acyclic anti - And syn-β-nitroamines with three contiguous stereocenters

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 1961-1971

  Anderson, James C ^a   Stepney, Gregory J ^b   Mills, Matthew R ^a   Horsfall, Lisa R ^a   Blake, Alexander J ^b   Lewis, William ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ASYMMETRIC ADDITION; C-C BONDS; CHIRAL LIGAND; CONTROLLED SYNTHESIS; DIASTEREO-SELECTIVITY; DIASTEREOISOMERS; ENANTIOSELECTIVE CONJUGATE ADDITION; HIGH YIELD; NITRO-MANNICH REACTION; NITROALKENES; NITROAMINES; REACTION CONDITIONS; REACTION MIXTURE; REACTION VESSEL; STEREOCENTERS; STRUCTURAL DIVERSITY; SYN-ISOMERS; TRANSITION STATE; VERSATILE PRODUCTS;

AROMATIC COMPOUNDS; ENANTIOSELECTIVITY; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ADDITION REACTIONS;

ALKENE DERIVATIVE; AMINE; BETA NITROAMINE; CARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; ISOMER; MANNICH REACTION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; COPPER; HYDROCARBONS, ACYCLIC; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; SOLVENTS; STEREOISOMERISM;

EID: 79953199764     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102408u     Document Type: Article

References (39)

1. Henry, L. Bull. Acad. R. Belg. 1896, 32, 33
2. For selected examples and references therein, see: Adams, H; Anderson, J. C.; Peace, S.; Pennell, A. M. K. J. Org. Chem. 1998, 63, 9932
3. Yamada, K.; Harwood, S. J.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504
4. Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgenson, K. A. J. Am. Chem. Soc. 2001, 123, 5843
5. Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625
6. Anderson, J. C.; Howell, G. P. J. Org. Chem. 2005, 70, 549
7. Bernardi, L.; Fini, F.; Herrera, R. P.; Ricci, A.; Sgarzani, V. Tetrahedron 2006, 62, 375
8. Singh, A.; Yoder, R. A.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2007, 129, 3466
9. Gomez-Bengoa, E.; Linden, A.; López, R.; Múgica-Mendiola, I.; Oiarbe, M.; Palomo, C. J. Am. Chem. Soc. 2008, 130, 7955
10. Wang, C.-J.; Dong, X.-Q.; Zhang, Z.-H.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606 For a review, see: Marqués-López, E.; Merino, P.; Tejero, T.; Herrera, R. P. Eur. J. Org. Chem. 2009, 2401
11. For the synthesis of fine chemicals from nitroalkanes, see: Ballini, R.; Palmieri, A.; Righi, P. Tetrahedron 2007, 63, 12099 For the synthesis of 1,2-diamines, see ref 2a and: Bernadi, L.; Bonini, B. F.; Capito, I. E.; Dessole, G.; Comes-Franchimi, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168
12. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294
13. Barrett, A. G. M.; Spilling, C. D. Tetrahedron Lett. 1998, 29, 5733
14. Sturgess, M. A.; Yarberry, D. J. Tetrahedron Lett. 1993, 34, 4743 For α-aminocarbonyl compounds, see: Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017
15. Handa, S.; Gnanadesikan, V.; Matsungaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900
16. Jiang, X.; Zhang, Y.; Wu, L.; Zhang, G.; Liu, X.; Zhang, H.; Fu, D.; Wang, R. Adv. Synth. Catal. 2009, 351, 2096
17. Handa, S.; Gnanadesikan, V.; Matsungaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 4925
18. Walser, A.; Benjamin, S. L. E.; Flynn, T.; Mason, C.; Schwartz, R.; Fryer, R. I. J. J. Org. Chem. 1978, 43, 936
19. Tsuritani, N.; Yamada, K.; Yoshikawa, N.; Shibasaki, M. Chem. Lett. 2002, 276
20. Pei, Z.; Li, X.; von Geldern, T. W.; Longnecker, D. P.; Stewart, K. D.; Backes, B. J.; Lai, C.; Lubben, T. H.; Ballaron, S. J.; Beno, D. W. A.; Kempf-Grote, A. J.; Sham, H. L.; Trevillyan, J. M. J. Med. Chem. 2007, 50, 1983
21. Xu, F.; Corley, E.; Murry, J. A.; Tschaen, D. M. Org. Lett. 2007, 9, 2669
22. Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 16632
23. Jakubec, P.; Helliwell, M.; Dixon, D. J. Org. Lett. 2008, 10, 4267
24. For acyclic examples, see: Howell, G. P.; Fletcher, S. P.; Geurts, K.; ter Horst, B.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 14977 and references cited therein.
25. For acyclic examples, see: Arai, T.; Yokoyama, N. Angew. Chem., Int. Ed. 2008, 47, 4989
26. For acyclic examples, see: Guo, S; Xie, Y.; Hu, X.; Xia, C.; Huang, H. Angew. Chem., Int. Ed. 2010, 49, 2728
27. Côté, A.; Linday, V. N. G.; Charette, A. B. Org. Lett. 2007, 9, 85
28. Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829
29. Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700
30. Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369
31. Anderson, J. C.; Howell, G. P.; Lawrence, R. M.; Wilson, C. S. J. Org. Chem. 2005, 70, 5665
32. Greene, T. W.; Wuts, P. G. M. Protective Groups In Organic Synthesis, 3 rd ed.; John Wiley & Sons, London, 1999.
33. Bellus, D.; Hrdlovic, P. Chem. Rev. 1967, 67, 599
34. Bellus, D.; Schaffner, K.; Higné, J. Helv. Chim. Acta 1968, 51, 1980
35. Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P. -Y.; Knochel, P. J. Org. Chem. 1996, 61, 1841
36. Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880
37. Similar analyses have been forwarded for diastereoselectivity in aldol reactions: Evans, D. A; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1
38. Heathcock, C. H. In Comprehensive Carbanion Chemistry, Part B; Elsevier: Amsterdam, 1984; p 177.
39. Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108