Hydroxyproline-derived pseudoenantiomeric [2.2.1] bicyclic phosphines: Asymmetric synthesis of (+)- and (-)-pyrrolines

Journal of the American Chemical Society

Volumn 136, Issue 34, 2014, Pages 11890-11893

  Henry, Christopher E ^a   Xu, Qihai ^a   Fan, Yi Chiao ^a   Martin, Tioga J ^a   Belding, Lee ^b   Dudding, Travis ^b   Kwon, Ohyun ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL OPERATIONS; HYDROXYPROLINE; STEREOCHEMISTRY;

ABSOLUTE CONFIGURATION; ASYMMETRIC SYNTHESIS; BICYCLIC PHOSPHINES; CHIRAL PHOSPHINE; L-PROLINE; NATURALLY OCCURRING; PYRROLINES;

PHOSPHORUS COMPOUNDS;

HEPTANE; HYDROXYPROLINE; IMINE; PHOSPHINE DERIVATIVE; PYRROLINE DERIVATIVE; BICYCLO COMPOUND; PYRROLE DERIVATIVE; PYRROLINE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHIRALITY; COLUMN CHROMATOGRAPHY; COVALENT BOND; DENSITY FUNCTIONAL THEORY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROBORATION; HYDROGEN BOND; PRECURSOR; PURIFICATION; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS; HYDROXYPROLINE; MOLECULAR STRUCTURE; PHOSPHINES; PYRROLES; STEREOISOMERISM;

EID: 84906751569     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja505592h     Document Type: Article

References (50)

1. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
2. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
3. Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520
4. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
5. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
6. Marinetti, A.; Voituriez, A. Synlett 2010, 174
7. Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005
8. Wang, S.-X.; Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Synlett 2011, 2766
9. Fan, Y. C.; Kwon, O. Phosphine Catalysis. In Science of Synthesis; List, B., Ed.; Georg Thieme: Stuttgart, 2012; Asymmetric Organocatalysis, Vol 1, Lewis Base and Acid Catalysts, pp 723-782.
10. Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724
11. Xu, S.; He, Z. RSC Adv. 2013, 3, 16885
12. Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588
13. Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927
14. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906
15. Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461
16. Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031
17. Zhu, X.-F.; Henry, C. E.; Kwon, O. Tetrahedron 2005, 61, 6276
18. Zhao, G.-L.; Shi, M. J. Org. Chem. 2005, 70, 9975
19. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836
20. Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426
21. Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988
22. Voituriez, A.; Panossian, A.; Fleury-Bregeot, N.; Retailleau, P.; Marinetti, A. J. Am. Chem. Soc. 2008, 130, 14030
23. Sampath, M.; Loh, T. P. Chem. Sci. 2010, 1, 739
24. Hua, X.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Angew. Chem., Int. Ed. 2010, 49, 4467
25. Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726
26. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293
27. Wang, D.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 2764
28. Steurer, M.; Jensen, K. L.; Worgull, D.; Jorgensen, K. A. Chem.-Eur. J. 2012, 18, 76
29. Marco-Martinez, J.; Marcos, V.; Reboredo, S.; Filippone, S.; Martin, N. Angew. Chem., Int. Ed. 2013, 52, 5115
30. Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141
31. Scherer, A.; Gladysz, J. A. Tetrahedron Lett. 2006, 47, 6335
32. Fleury-Bregeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron 2007, 63, 11920
33. Panossian, A.; Fleury-Bregeot, N.; Marinetti, A. Eur. J. Org. Chem. 2008, 22, 3826
34. Pinto, N.; Fleury-Bregeot, N.; Marinetti, A. Eur. J. Org. Chem. 2009, 23, 146
35. Fang, Y.-Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660
36. Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767
37. Chawla, A. S.; Redha, F. M.; Jackson, A. H. Phytochemistry 1985, 24, 1821
38. Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669
39. Wager, T. T.; Welch, W.; O'Neill, B. T. NK1 Antagonist, WO Patent 2004/110996, December 23, 2004.
40. Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; De Leon, P.; Tamanoi, F.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 5843
41. Watanabe, M.; Fiji, H. D. G.; Guo, L.; Chan, L.; Kinderman, S. S.; Slamon, D. J.; Kwon, O.; Tamanoi, F. J. Biol. Chem. 2008, 283, 9571
42. Lu, J.; Chan, L.; Fiji, H. D. G.; Dahl, R.; Kwon, O.; Tamanoi, F. Mol. Cancer Ther. 2009, 8, 1218
43. Zimonjic, D. B.; Chan, L. N.; Tripathi, V.; Lu, J.; Kwon, O.; Popescu, N. C.; Lowy, D. R.; Tamanoi, F. BMC Cancer 2013, 13, 198
44. The chiral phosphine 3 ′ has been employed previously in a successful asymmetric [3 + 2] annulation between a γ-ethylallenoate and an imine derived from indole-3-carboxaldehyde. This report does not, however, contain any information about the synthesis and characterization of 3 ′; see: Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510
45. 2-symmetric diol of ∼83%: Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449
46. No purification was necessary, except for recrystallization of the final product 1; the reaction was readily run on a 100-g scale: Braish, T. F.; Fox, D. E. J. Org. Chem. 1990, 55, 1684
47. Imamoto, T. Pure Appl. Chem. 1993, 65, 655
48. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295
49. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373
50. imine bond formations are possible; using our previous findings as a starting point, we were, however, able to generate a total of 32 viable low-energy modes of addition for each entry. For specific details, see the SI and Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643