Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6503-6509

  Yang, Xiao Fei ^a   Yu, Wei Hua ^c   Ding, Chang Hua ^a   Ding, Qiu Ping ^c   Wan, Shi Li ^a   Hou, Xue Long ^a,b   Dai, Li Xin ^a   Wang, Pin Jie ^a  

^a Laboratory of Organometallic Chemistry Shanghai   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTRATES; AMINO ACID DERIVATIVES; ASYMMETRIC ALLYLIC ALKYLATIONS; ENANTIOSELECTIVE ALLYLATION; OPTICALLY ACTIVE; ORGANIC SYNTHESIS; PALLADIUM-CATALYZED; TETRAHYDROPYRIDINE;

ALLYLATION; AMINO ACIDS; CATALYSIS; PARAFFINS;

ENANTIOSELECTIVITY;

AMINO ACID DERIVATIVE; NITROALKANE; PALLADIUM; PYRIDINE DERIVATIVE; ALKANE; ALLYL COMPOUND; ALLYLAMINE; AMINO ACID; NITRO DERIVATIVE; ORGANOMETALLIC COMPOUND;

ALLYLATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; SUBSTITUTION REACTION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKANES; ALLYL COMPOUNDS; ALLYLAMINE; AMINO ACIDS; CATALYSIS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84880025762     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400663d     Document Type: Article

References (33)

1. Barrett, A. G. M.; Grabowski, G. G. Chem. Rev. 1986, 86, 751
2. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001.
3. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 12, 1877
4. Roca-Lopez, D.; Sadaba, D.; Delso, I.; Herrera, R. P.; Tejero, T.; Merino, P. Tetrahedron: Asymmetry 2010, 21, 2561
5. Noble, A.; Anderson, J. C. Chem. Rev. 2013, 113, 2887
6. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418
7. Chinchilla, R.; Nájera, C.; Sánchez-Agulló, P. Tetrahedron: Asymmetry 1994, 5, 1393
8. Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 2054
9. Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861
10. Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929
11. Liu, X.; Jiang, J.; Shi, M. Tetrahedron: Asymmetry 2007, 18, 2773
12. Uraguchi, D.; Sakaki, S.; Ooi, T. J. Am. Chem. Soc. 2007, 129, 12392
13. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
14. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258
15. Ding, C.-H.; Hou, X.-L. Top. Organomet. Chem. 2011, 36, 247
16. Geneît, J. P.; Grisoni, S. Tetrahedron Lett. 1988, 36, 4543
17. Rieck, H.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2687
18. Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2000, 39, 3122
19. Trost, B. M.; Surivet, J.-P. J. Am. Chem. Soc. 2000, 122, 6291
20. Nemoto, T.; Jin, L.; Nakamura, H.; Hamada, Y. Tetrahedron Lett. 2006, 47, 6577
21. Uozumi, Y.; Suzuki, T. J. Org. Chem. 2006, 71, 8644
22. Maki, K.; Kanai, M.; Shibasaki, M. Tetrahedron 2007, 63, 4250
23. Nemoto, T.; Hamada, Y. J. Synth. Org. Chem., Jpn. 2011, 69, 763
24. Trost, B. M.; Jiang, C. J. Am. Chem. Soc. 2001, 123, 12907
25. For Ir-catalyzed asymmetric allylic alkylation of nitro compounds, see the following: Dahnz, A.; Helmchen, G. Synlett 2006, 697
26. You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471
27. Sun, N.; Hou, X.-L. Org. Lett. 2004, 6, 4399
28. Zheng, W.-H.; Sun, N.; Hou, X.-L. Org. Lett. 2005, 7, 5151
29. Zheng, W.-H.; Zheng, B.-H.; Zhang, Y.; Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718
30. Zhang, K.; Peng, Q.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2008, 47, 1741
31. Chen, J.-P.; Ding, C.-H.; Liu, W.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493
32. Zheng, B.-H.; Ding, C.-H.; Hou, X.-L. Synlett 2011, 2262
33. Yang, X.-F.; Ding, C.-H.; Li, X.-H.; Huang, J.-Q.; Hou, X.-L.; Dai, L.-X.; Wang, P.-J. J. Org. Chem. 2012, 77, 8980