Chiral integrated catalysts composed of bifunctional thiourea and arylboronic acid: Asymmetric aza-Michael addition of α,β-unsaturated carboxylic acids

Chemical and Pharmaceutical Bulletin

Volumn 64, Issue 7, 2016, Pages 704-717

  Hayama, Noboru ^a   Azuma, Takumi ^a   Kobayashi, Yusuke ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Arylboronic acid; Aza Michael addition; Integrated catalyst; O benzylhydroxylamine; Thiourea; , unsaturated carboxylic acid

Indexed keywords

1,2 DIAMINE DERIVATIVE; AMINO ACID DERIVATIVE; ARYLBORONIC ACID; BETA AMINO ACID; BORONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAMINE DERIVATIVE; NITROGEN; NUCLEOPHILE; THIOUREA; UNCLASSIFIED DRUG; AMINO ACID; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL COMPOSITION; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; OPTICS; REACTION ANALYSIS; STEREOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; AZA COMPOUNDS; BORONIC ACIDS; CARBOXYLIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; THIOUREA;

EID: 84978137335     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c15-00983     Document Type: Article

References (32)

1. Krishna P. R., Sreeshailam A., Srinivas R., Tetrahedron, 65, 9657-9672 (2009).
2. Enders D., Wang C., Liebich J. X., Chem. Eur. J., 15, 11058-11076 (2009).
3. Weiner B., Szymański W., Janssen D. B., Minnaard A. J., Feringa B. L., Chem. Soc. Rev., 39, 1656-1691 (2010).
4. Wang J., Li P., Choy P. Y., Chan A. S. C., Kwong F. Y., ChemCatChem, 4, 917-925 (2012).
5. Ballerini E., Curini M., Gelman D., Lanari D., Piermatti O., Pizzo F., Santoro S., Vaccaro L., ACS Sustainable Chem. Eng., 3, 1221-1226 (2015), and references therein.
6. Weiß M., Borchert S., Rémond E., Jugé S., Gröger H., Heteroatom. Chem., 23, 202-209 (2012).
7. Kobayashi Y., Taniguchi Y., Hayama N., Inokuma T., Takemoto Y., Angew. Chem. Int. Ed., 52, 11114-11118 (2013).
8. Monge D., Jiang H., Alvarez-Casao Y., Chem. Eur. J., 21, 4494-4504 (2015).
9. Hamashima Y., Somei H., Shimura Y., Tamura T., Sodeoka M., Org. Lett., 6, 1861-1864 (2004).
10. Kikuchi S., Sato H., Fukuzawa S., Synlett, 2006, 1023-1026 (2006).
11. Yamagiwa N., Qin H., Matsunaga S., Shibasaki M., J. Am. Chem. Soc., 127, 13419-13427 (2005).
12. Sibi M. P., Itoh K., J. Am. Chem. Soc., 129, 8064-8065 (2007).
13. Wu B., Szymanski W., Wietzes P., de Wildeman S., Poelarends G. J., Feringa B. L., Janssen D. B., ChemBioChem, 10, 338-344 (2009).
14. Weise N. J., Parmeggiani F., Ahmed S. T., Turner N. J., J. Am. Chem. Soc., 137, 12977-12983 (2015).
15. Maki T., Ishihara K., Yamamoto H., Tetrahedron, 63, 8645-8657 (2007).
16. Arnold K., Davies B., Giles R. L., Grosjean C., Smith G. E., Whiting A., Adv. Synth. Catal., 348, 813-820 (2006).
17. Gernigon N., Al-Zoubi R. M., Hall D. G., J. Org. Chem., 77, 8386-8400 (2012).
18. Mohy El Dine T., Erb W., Berhault Y., Rouden J., Blanchet J., J. Org. Chem., 80, 4532-4544 (2015).
19. Furuta K., Miwa Y., Iwanaga K., Yamamoto H., J. Am. Chem. Soc., 110, 6254-6255 (1988).
20. Al-Zoubi R. M., Marion O., Hall D. G., Angew. Chem. Int. Ed., 47, 2876-2879 (2008).
21. Zheng H., McDonald R., Hall D. G., Chem. Eur. J., 16, 5454-5460 (2010).
22. Mo X., Yakiwchuk J., Dansereau J., McCubbin J. A., Hall D. G., J. Am. Chem. Soc., 137, 9694-9703 (2015).
23. Aelvoet K., Batsanov A. S., Blatch A. J., Grosjean C., Patrick L. G. F., Smethurst C. A., Whiting A., Angew. Chem. Int. Ed., 47, 768-770 (2008).
24. Hashimoto T., Gálves A. O., Maruoka K., J. Am. Chem. Soc., 135, 17667-17670 (2013).
25. Morita Y., Yamamoto T., Nagai H., Shimizu Y., Kanai M., J. Am. Chem. Soc., 137, 7075-7078 (2015).
26. Azuma T., Murata A., Kobayashi Y., Inokuma T., Takemoto Y., Org. Lett., 16, 4256-4259 (2014).
27. Takemoto Y., Chem. Pharm. Bull., 58, 593-601 (2010).
28. De C. K., Klauber E. G., Seidel D., J. Am. Chem. Soc., 131, 17060-17061 (2009).
29. Klausen R. S., Jacobsen E. N., Org. Lett., 11, 887-890 (2009).
30. The absolute configurations of 2a, 2b, 8, and 10 were assigned as S by comparison of their specific optical rotations with those of authentic samples (see Charts S1 and S2 in the Supplementary Materials).
31. Marcelli T., Angew. Chem. Int. Ed., 49, 6840-6843 (2010).
32. Seto Y., Takahashi K., Matsuura H., Kogami Y., Yada H., Yoshihara T., Nabeta K., Biosci. Biotechnol. Biochem., 71, 1470-1475 (2007).