Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Brønsted acid

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1048-1051

  Yamanaka, Takuto ^a   Kondoh, Azusa ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; THERMODYNAMICS;

ACETALIZATION; ENANTIOSELECTIVE; ENOL ETHERS; HYDROXY GROUPS; KINETIC RESOLUTION; RACEMIC SECONDARY ALCOHOLS;

KINETICS;

AMINOALCOHOL; BRONSTED ACID; HYDROXYL GROUP; PHOSPHORIC ACID;

ACETALIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; ESTERIFICATION; KINETIC RESOLUTION; RACEMIC MIXTURE; THERMODYNAMICS;

EID: 84921963147     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512238n     Document Type: Article

References (42)

1. (a) Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. In Topics in Stereochemistry; John Wiley & Sons, Inc.: New York, 1988; Vol. 18, p 249.
2. (b) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407-1446.
3. (c) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974-4001.
4. (d) Ahmed, M.; Kelly, T.; Ghanem, A. Tetrahedron 2012, 68, 6781-6802.
5. (a) Wurz, R. P. Chem. Rev. 2007, 107, 5570-5595.
6. (b) Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012-6042.
7. (c) Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613-1666.
8. Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons, Inc.: New York, 2007.
9. (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566-1568.
10. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356-5357.
11. (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520-1543.
12. (b) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743.
13. (c) Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
14. (d) Yamamoto, H.; Payette, N. In Hydrogen Bonding in Organic Synthesis; Pihko, P. M., Ed.; Wiley-VCH: Weinheim, 2009; pp 73-140.
15. (e) Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395-456.
16. (a) Terada, M. Chem. Commun. 2008, 4097-4112.
17. (b) Terada, M. Synthesis 2010, 1929-1982.
18. (c) Terada, M. Bull. Chem. Soc. Jpn. 2010, 101-119.
19. (d) Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. B. Org. Biomol. Chem. 2010, 8, 5262-5276.
20. (e) Akiyama, T. In Science of Synthesis, Asymmetric Organocatalysis 2, Brønsted Base and Acid Catalysts, and Additional Topics; Maruoka, K., Ed.; Georg Thieme Verlag KG: New York, 2012; Vol. 2, pp 169-217.
21. (f) Terada, M.; Momiyama, N. In Science of Synthesis, Asymmetric Organocatalysis 2, Brønsted Base and Acid Catalysts, and Additional Topics; Maruoka, K., Ed.; Georg Thieme Verlag KG: New York, 2012; Vol. 2, pp 219-296.
22. (g) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047-9153.
23. (a) Čorić, I.; Vellalath, S.; List, B. J. Am. Chem. Soc. 2010, 132, 8536-8537.
24. (b) Čorić, I.; Müller, S.; List, B. J. Am. Chem. Soc. 2010, 132, 17370-17373.
25. (c) Čorić, I.; List, B. Nature 2012, 483, 315-319.
26. (d) Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P. J. Am. Chem. Soc. 2012, 134, 8074-8077.
27. (e) Nagorny, P.; Sun, Z.; Winschel, G. A. Synlett 2013, 24, 661-665.
28. (f) Kim, J. H.; Čorić, I.; Vellalath, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 4474-4477.
29. (g) Chen, Z.; Sun, J. Angew. Chem., Int. Ed. 2013, 52, 13593-13596.
30. Mensah, E.; Camasso, N.; Kaplan, W.; Nagorny, P. Angew. Chem., Int. Ed. 2013, 52, 12932-12936.
31. As shown in the following scheme, the formed acetal is thermodynamically much more stable than the alcohol and enol ether.
32. (a) Mandai, H.; Murota, K.; Mitsudo, K.; Suga, S. Org. Lett. 2012, 14, 3486-3489.
33. (b) Harada, S.; Kuwano, S.; Yamaoka, Y.; Yamada, K.; Takasu, K. Angew. Chem., Int. Ed. 2013, 52, 10227-10230.
34. Screening of enol ethers was also conducted. See Supporting Information (SI) in details.
35. Screening of chiral phosphoric acids was also conducted. See SI in details.
36. Schoepf, C.; Wuest, W. Justus Liebigs Ann. Chem. 1959, 626, 150-154.
37. Formed acetal 4e was obtained as a ca. 1:1 diastereomeric mixture.
38. Other factors that caused the reduction of the s value at high concentration also cannot be ruled out at this point.
39. The acetalization rate was reproduced well in the presence of MS 4A.
40. (R)-1a was employed instead of (R)-1b, because the acetalization rate of (R)-1a was higher than that of (R)-1b in those substrates without any detrimental effect on the individual s values.
41. Application of the resolution system to a racemic 1,3-amino alcohol as well as the substrate possessing a tertiary alkyl amine moiety resulted in the low s values. See SI in details.
42. Plausible structures of the intramolecular hydrogen bonding models of 2e and 5 are illustrated in the SI.