Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters

Angewandte Chemie - International Edition

Volumn 55, Issue 46, 2016, Pages 14417-14421

  Alam, Rauful ^a   Diner, Colin ^a   Jonker, Sybrand ^a   Eriksson, Lars ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

allylboration; asymmetric catalysis; indoles; organocatalysis; stereoselectivity

Indexed keywords

CATALYSIS;

ALLYLBORATION; ASYMMETRIC CATALYSIS; CONTIGUOUS STEREOCENTERS; DIHYDROISOQUINOLINES; HIGH STEREOSELECTIVITIES; INDOLES; ORGANOCATALYSIS; STEREODIVERGENT SYNTHESIS;

STEREOSELECTIVITY;

EID: 84991394209     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201608605     Document Type: Article

References (40)

1. D. G. Hall, Boronic Acids, Wiley, Weinheim, 2011;
2. D. G. Hall, H. Lachance, Allylboration of Carbonyl Compounds, Wiley, Hoboken, 2012.
3. R. Alam, T. Vollgraff, L. Eriksson, K. J. Szabó, J. Am. Chem. Soc. 2015, 137, 11262.
4. A. B. Charette, Chiral Amine Synthesis, Wiley-VCH, Weinheim, 2010.
5. M. Yus, J. C. González-Gómez, F. Foubelo, Chem. Rev. 2013, 113, 5595;
6. M. Sugiura, K. Hirano, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7182;
7. R. Alam, A. Das, G. Huang, L. Eriksson, F. Himo, K. J. Szabó, Chem. Sci. 2014, 5, 2732;
8. A. Das, R. Alam, L. Eriksson, K. J. Szabó, Org. Lett. 2014, 16, 3808;
9. B. Dhudshia, J. Tiburcio, A. N. Thadani, Chem. Commun. 2005, 5551;
10. P. G. M. Wuts, Y. W. Jung, J. Org. Chem. 1991, 56, 365.
11. J. D. Sieber, J. P. Morken, J. Am. Chem. Soc. 2006, 128, 74;
12. T. R. Wu, J. M. Chong, J. Am. Chem. Soc. 2006, 128, 9646;
13. R. Wada, T. Shibuguchi, S. Makino, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 7687;
14. E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 3332;
15. A. Chakrabarti, H. Konishi, M. Yamaguchi, U. Schneider, S. Kobayashi, Angew. Chem. Int. Ed. 2010, 49, 1838;
16. Angew. Chem. 2010, 122, 1882;
17. F. W. van der Mei, H. Miyamoto, D. L. Silverio, A. H. Hoveyda, Angew. Chem. Int. Ed. 2016, 55, 4701;
18. Angew. Chem. 2016, 128, 4779;
19. J. L. Y. Chen, V. K. Aggarwal, Angew. Chem. Int. Ed. 2014, 53, 10992;
20. Angew. Chem. 2014, 126, 11172.
21. F. Nowrouzi, R. A. Batey, Angew. Chem. Int. Ed. 2013, 52, 892;
22. Angew. Chem. 2013, 125, 926.
23. Y. N. Bubnov, I. V. Zhun, E. V. Klimkina, A. V. Ignatenko, Z. A. Starikova, Eur. J. Org. Chem. 2000, 3323.
24. S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc. 2007, 129, 15398.
25. P. Jain, J. C. Antilla, J. Am. Chem. Soc. 2010, 132, 11884;
26. P. Jain, H. Wang, K. N. Houk, J. C. Antilla, Angew. Chem. Int. Ed. 2012, 51, 1391;
27. Angew. Chem. 2012, 124, 1420.
28. S.-L. Shi, Z. L. Wong, S. L. Buchwald, Nature 2016, 532, 353.
29. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065.
30. H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007;
31. Y. Lian, H. M. L. Davies, J. Am. Chem. Soc. 2010, 132, 440;
32. S. Rendler, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 5027.
33. H. E. Zimmerman, M. D. Traxler, J. Am. Chem. Soc. 1957, 79, 1920;
34. M. M. Midland, S. B. Preston, J. Am. Chem. Soc. 1982, 104, 2330;
35. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1982, 21, 555;
36. Angew. Chem. 1982, 94, 569.
37. A. I. Meyers, D. A. Dickman, M. Boes, Tetrahedron 1987, 43, 5095;
38. A. I. Meyers, M. Boes, D. A. Dickman, Angew. Chem. Int. Ed. Engl. 1984, 23, 458;
39. Angew. Chem. 1984, 96, 448.
40. H. Noda, J. W. Bode, J. Am. Chem. Soc. 2015, 137, 3958.