Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes

Journal of the American Chemical Society

Volumn 137, Issue 19, 2015, Pages 6176-6179

  Joannou, Matthew V ^a   Moyer, Brandon S ^a   Meek, Simon J ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES;

ABSOLUTE STEREOCHEMISTRY; COPPER COMPLEXES; DIASTEREOSELECTIVE SYNTHESIS; ENANTIO; MONODENTATES; PHOSPHORAMIDITES; STEREOGENIC CENTERS; VINYL ALDEHYDE;

STEREOSELECTIVITY;

1,2 HYDROXYBORONATE DERIVATIVE; ALDEHYDE; ALKYL GROUP; BORONIC ACID DERIVATIVE; COPPER; COPPER COMPLEX; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOMERIC RATIO; ENANTIOSELECTIVITY; MECHANICS; STEREOCHEMISTRY; SYNTHESIS; ALKYLATION; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM;

ALDEHYDES; ALKYLATION; BORONIC ACIDS; CATALYSIS; COPPER; HYDROXYLATION; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM;

EID: 84930222017     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03477     Document Type: Article

References (48)

1. Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
2. Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695-4712
3. Carroll, A.- M.; O'Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609-631
4. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160-3161
5. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062-6064
6. Smith, S. M.; Takacs, J. M. J. Am. Chem. Soc. 2010, 132, 1740-1741
7. Sasaki, Y.; Zhong, C.; Sawamura, M.; Ito, H. J. Am. Chem. Soc. 2010, 132, 1226-1227
8. Corberán, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2011, 50, 7079-7082
9. Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989-3992
10. Lee, H.; Lee, B. Y.; Yun, J. Org. Lett. 2015, 17, 764-766
11. For a recent review on Cu-catalyzed boryl addition reactions, see: Semba, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Tetrahedron 2015, 71, 2183-2197
12. Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717-4725
13. Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134-9135
14. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234-18235
15. Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 13210-13211
16. Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222-11231
17. Toribatake, K.; Nishiyama, H. Angew. Chem., Int. Ed. 2013, 52, 11011-11015
18. Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386-390
19. Coombs, J. R.; Zhang, L.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 16140-16143
20. Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856-14857
21. Guzman-Martinez, A.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10634-10637
22. Ito, H.; Kunii, S.; Sawamura, M. Nat. Chem. 2010, 2, 972-976
23. Park, J. K.; Lackey, H. H.; Ondrusek, B. A.; McQuade, D. T. J. Am. Chem. Soc. 2011, 133, 2410-2413
24. Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145-147
25. Chen, I.-H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664-11665
26. Chea, H.; Sim, H.-S.; Yun, J. Adv. Synth. Catal. 2009, 351, 855-858
27. Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008-5011
28. Chen, I.-H.; Kanai, M.; Shibasaki, M. Org. Lett. 2010, 12, 4098-4101
29. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894-899
30. O'Brien, J. M.; Lee, K.-S.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10630-10633
31. Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277-8285
32. Radomkit, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 3387-3391
33. Nelson, H. M.; Williams, B. D.; Miró, J.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 3213-3216
34. Knochel, P. J. Am. Chem. Soc. 1990, 112, 7431-7433
35. Waas, J. R.; Sidduri, A. R.; Knochel, P. Tetrahedron Lett. 1992, 33, 3717-3720
36. Sakai, M.; Saito, S.; Kanai, G.; Suzuki, A.; Miyaura, N. Tetrahedron 1996, 52, 915-924
37. Matteson, D. S.; Moody, R. J. J. Am. Chem. Soc. 1977, 99, 3196-3197
38. Matteson, D. S.; Arne, K. J. Am. Chem. Soc. 1978, 100, 1325-1326
39. Matteson, D. S.; Moody, R. J. Organometallics 1982, 1, 20-28
40. Pelter, A.; Singaram, B.; Williams, L.; Wilson, J. W. Tetrahedron Lett. 1983, 24, 623-626
41. Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581-10584
42. Endo, K.; Ohkubo, T.; Hirokami, M.; Shibata, T. J. Am. Chem. Soc. 2010, 132, 11033-11035
43. Endo, K.; Ohkubo, T.; Shibata, T. Org. Lett. 2011, 13, 3368-3371
44. Endo, K.; Ohkubo, T.; Ishioka, T.; Shibata, T. J. Org. Chem. 2012, 77, 4826-4831
45. Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534-6537
46. Potter, B.; Szymaniak, A. A.; Edelstein, E. K.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 17918-17921
47. Palimkar, S. S.; Uenishi, J. Org. Lett. 2010, 12, 4160-4163
48. Mlynarski, S. N.; Karns, A. S.; Morken, J. P. J. Am. Chem. Soc. 2012, 134, 16449-16451