Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions

Journal of the American Chemical Society

Volumn 137, Issue 22, 2015, Pages 7075-7078

  Morita, Yuya ^a   Yamamoto, Tomohiro ^a   Nagai, Hideoki ^a   Shimizu, Yohei ^a   Kanai, Motomu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBOXYLIC ACIDS; CATALYSTS; CHEMICAL ACTIVATION; FUNCTIONAL GROUPS; KETONES;

CARBON NUCLEOPHILES; CATALYTIC ACTIVATION; CATALYTIC METHODS; ENANTIOSELECTIVE; MANNICH-TYPE REACTIONS; NUCLEOPHILIC ACTIVATION; ORGANIC MOLECULES; SYNTHETIC METHODS;

BORON;

AMIDE; BORON; CARBONYL DERIVATIVE; CARBOXYLIC ACID; ESTER; FUNCTIONAL GROUP; KETONE; NUCLEOPHILE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; MANNICH REACTION; NUCLEOPHILICITY; CHEMISTRY;

BORON; CARBOXYLIC ACIDS; CATALYSIS;

EID: 84935859931     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04175     Document Type: Article

References (33)

1. Rao, P. P. N.; Kabir, S. N.; Mohamed, T. Pharmaceuticals 2010, 3, 1530
2. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Häbich, D. Angew. Chem., Int. Ed. 2006, 45, 5072
3. Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 5767
4. Rosen, B. R.; Simke, L. R.; Thuy-Boun, P. S.; Dixon, D. D.; Yu, J.-Q.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 7317
5. Robles, O.; Romo, D. Nat. Prod. Rep. 2014, 31, 318
6. Trost, B. M. Science 1991, 254, 1471
7. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40
8. Furuta, K.; Miwa, Y.; Iwanaga, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 6254
9. Al-Zoubi, R. M.; Marion, O.; Hall, D. G. Angew. Chem., Int. Ed. 2008, 47, 2876
10. Zheng, H.; McDonald, R.; Hall, D. G. Chem.-Eur. J. 2010, 16, 5454
11. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196
12. Maki, T.; Ishihara, K.; Yamamoto, H. Tetrahedron 2007, 63, 8645
13. Gernigon, N.; Al-Zoubi, R. M.; Hall, D. G. J. Org. Chem. 2012, 77, 8386
14. Charville, H.; Jackson, D.; Hodges, G.; Whiting, A. Chem. Commun. 2010, 46, 1813
15. Nelson, P.; Pelter, A. J. Chem. Soc. 1965, 5, 142
16. Lee, D.; Newman, S. G.; Taylor, M. S. Org. Lett. 2009, 11, 5486
17. Stivala, C. E.; Zakarian, A. J. Am. Chem. Soc. 2011, 133, 11936
18. Ma, Y.; Stivala, C. E.; Wright, A. M.; Hayton, T.; Liang, J.; Kersztes, I.; Lobkovsky, E.; Collum, D. B.; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 16853
19. Lu, P.; Jackson, J. J.; Eickhoff, J. A.; Zakarian, A. J. Am. Chem. Soc. 2015, 137, 656
20. Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111
21. Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099
22. Downey, C. W.; Johnson, M. W.; Lawrence, D. H.; Fleisher, A. S.; Tracy, K. J. J. Org. Chem. 2010, 75, 5351
23. Ramachandran, P. V.; Chanda, P. M.; Otoo, B. Tetrahedron Lett. 2014, 55, 1289
24. The relative configurations of the products were determined after conversion to known compounds (see SI).
25. a values are described in the SI.
26. Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797
27. Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29
28. Karimi, B.; Enders, D.; Jafari, E. Synthesis 2013, 45, 2769
29. Suzuki, Y.; Yazaki, R.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2009, 48, 5026
30. Kobayashi, S.; Kiyohara, H.; Yamaguchi, M. J. Am. Chem. Soc. 2011, 133, 708
31. The absolute configurations of the products were determined after conversion to known compounds (see SI).
32. Enders, D.; Seppelt, M.; Beck, T. Adv. Synth. Catal. 2010, 352, 1413
33. Isolated boron tripropionate reacted with imine 2a, producing 3aa in high to moderate yield under the standard reaction conditions. This result supports our hypothesis that acyloxyborane is an active intermediate for the reaction (see SI).