Kinetic Resolution of Unsymmetrical Acyclic Allyl Carbonates Using Trimethylsilyl Cyanide via Palladium-Catalyzed Asymmetric Allylic Alkylation

Synlett

Volumn 26, Issue 11, 2015, Pages 1510-1514

  Bai, Da Chang ^a   Wang, Wan Ying ^a   Ding, Chang Hua ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

asymmetric allylic alkylation; kinetic resolution; palladium; trimethylsilyl cyanide; unsymmetrical acylic allyl carbonates

Indexed keywords

ACYCLIC ALLYL CARBONATE DERIVATIVE; CARBONIC ACID DERIVATIVE; CYANIDE; NITRILE; PALLADIUM; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CYANATION; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 84931955144     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1378709     Document Type: Article

References (54)

1. Rappoport Z. The Chemistry of the Cyano Group. Interscience Publishers London: 1970
2. Larock R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations. VCH New York: 1989
3. Najera C., Sansano J. M. Chem. Rev.: 2007; 107 4584
4. Ordñez M., Cativiela C. Tetrahedron: Asymmetry: 2007; 18 3
5. Metz A. E., Kozlowski M. C. J. Org. Chem.: 2015; 80 1
6. Huang J. K., Haar C. M., Nolan S. P., Marcone J. E., Moloy K. G. Organometallics: 1999; 18 297
7. Zapf A., Beller M. Top. Catal.: 2002; 19 101
8. Fleming F. F., Yao L. H., Ravikumar P. C., Funk L., Shook B. C. J. Med. Chem.: 2010; 53 7902
9. Jiang W., Liu H. Chin. J. Org. Chem.: 2012; 32 1643
10. Enders D., Shilvock J. P. Chem. Soc. Rev.: 2000; 29 359
11. Gröger H. Chem. Rev.: 2003; 103 2795
12. Khan N. H., Kureshy R. I., Abdi S. H. R, Agrawal S., Jasra R. V. Coord. Chem. Rev.: 2008; 252 593
13. North M., Usanov D. L., Young C. Chem. Rev.: 2008; 108 5146
14. Salter M. M., Fossey J. S., Mori Y., Kobayashi S. Chem. Rev.: 2011; 111 2626
15. Wang J., Liu X., Feng X. Chem. Rev.: 2011; 111 6947
16. Ohkuma T., Kurono N. Synlett: 2012; 23 1865
17. Trost B. M., Van Vranken D. L. Chem. Rev.: 1996; 96 395
18. Trost B. M., Crawley M. L. Chem. Rev.: 2003; 103 2921
19. Lu Z., Ma S. Angew. Chem. Int. Ed.: 2008; 47 258
20. Ding C.-H, Hou X.-L. Top. Organomet. Chem.: 2011; 36 247
21. You S.-L, Zhu X.-Z, Luo Y.-M, Hou X.-L, Dai L.-X. J. Am. Chem. Soc.: 2001; 123 7471
22. Cheng H.-B, Feng B., Chen L.-Y, Guo W., Yu X.-Y, Lu L.-Q, Chen J.-R, Xiao W.-J. Chem. Commun.: 2014; 50 2873
23. Feng B., Cheng H.-B, Chen J.-R, Deng Q.-H, Lu L.-Q, Xiao W.-J. Chem. Commun.: 2014; 50 9550
24. Yang H., Zhou H., Yin H., Xia C., Jiang G. Synlett: 2014; 25 2149
25. Baeza A., Nájera C. Synthesis: 2014; 46 25
26. Alberch E., Brook C., Asad S. A., Shevyrev M., Ulicki J. S., Hossain M. M. Synlett: 2015; 26 388
27. Chen T.-G, Fang P., Hou X.-L, Dai L.-X. Synthesis: 2015; 47 134
28. Kagan H. B., Fiaud J. C. Top. Stereochem.: 1988; 18 249
29. Cook G. R. Curr. Org. Chem.: 2000; 4 869
30. Keith J. M., Larrow J. F., Jacobsen E. N. Adv. Synth. Catal.: 2001; 343 5
31. Vedejs E., Jure M. Angew. Chem. Int. Ed.: 2005; 44 3974
32. Hayashi T., Yamamoto A., Ito Y. J. Chem. Soc., Chem. Commun.: 1986; 1090
33. Kagan H. B., Fiaud J. C. Top. Stereochem.: 1988; 18 249
34. Gais H.-J, Spalthoff N., Jagusch T., Frank M., Raabe G. Tetrahedron Lett.: 2000; 41 3809
35. Longmire J. M., Wang B., Zhang X. Tetrahedron Lett.: 2000; 41 5435
36. Hughes D. L., Palucki M., Yasuda N., Reamer R. A., Reider P. J. J. Org. Chem.: 2002; 67 2762
37. Lussem B. J., Gais H. J. J. Am. Chem. Soc.: 2003; 125 6066
38. Faller J. W., Wilt J. C., Parr J. Org. Lett.: 2004; 6 1301
39. Fischer C., Defieber C., Suzuki T., Carreira E. M. J. Am. Chem. Soc.: 2004; 126 1628
40. Onitsuka K., Matsushima Y., Takahashi S. Organometallics: 2005; 24 6472
41. Mao B., Ji Y.-N, Fañanás-Mastral M., Auke-Meetsma G. C., Feringa B. L. Angew. Chem. Int. Ed.: 2012; 51 3168
42. Lei B.-L, Ding C.-H, Yang X.-F, Wan X.-L, Hou X.-L. J. Am. Chem. Soc.: 2009; 131 18250
43. Hou X.-L, Zheng B.-H. Org. Lett.: 2009; 11 1789
44. Lei B.-L, Zhang Q.-S, Yu W.-H, Ding Q.-P, Ding C.-H, Hou X.-L. Org. Lett.: 2014; 16 1944
45. Tsuji Y., Yamada N., Tanaka S. J. Org. Chem.: 1993; 58 16
46. Tsuji Y., Kusui T., Kojima T., Sugiura Y., Yamada N., Tanaka S., Ebihara M., Kawamura T. Organometallics: 1998; 17 4835
47. Munemori M., Tsuji H., Uchida K., Suzuki Y., Isa K., Minakawa M., Kawatsura M. Synthesis: 2014; 46 2747
48. Saha B., RajanBabu T. V. Org. Lett.: 2006; 8 4657
49. Li D. R., He A., Falck J. R. Org. Lett.: 2010; 12 1756
50. Akai S., Hanada R., Fujiwara N., Kita Y., Egi M. Org. Lett.: 2010; 12 4900
51. He P., Liu X.-H, Zheng H.-F, Li W., Lin L.-L, Feng X.-M. Org. Lett.: 2012; 14 5134
52. Fontana G., Lubineau A., Scherrmann M. C. Org. Biomol. Chem.: 2005; 3 1375
53. Trost B. M., Xu J., Schmidt T. J. Am. Chem. Soc.: 2009; 131 18343
54. Sha S.-C, Zhang J.-D, Carroll P. J., Walsh P. J. J. Am. Chem. Soc.: 2013; 135 17602