Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Highly Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Novel Chiral tert-Amino Alcohols

  • Zhang, Cong-Hai (Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University) ;
  • Yan, Sheng-Jiao (Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University) ;
  • Pan, Sheng-Qiang (Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University) ;
  • Huang, Rong (Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University) ;
  • Lin, Jun (Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University)
  • Published : 2010.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

A series of novel chiral tert-amino alcohols 4a-h derived from enantiomerically pure phenylalanine were synthesized efficiently and used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc (diethylzinc-to-aldehyde addition). The use of 10 mol % of the amino alcohols led to the corresponding sec-alcohols with excellent enantioselectivities (up to 100% ee) and high yields.

Keywords

References

  1. Joshi, S. N.; Malhotra, S. V. Tetrahedron: Asymmetry 2003, 14,1763. https://doi.org/10.1016/S0957-4166(03)00347-1
  2. Dai, W. M.; Zhu, H. J.; Hao, X. J. Tetrahedron: Asymmetry1995, 6, 1857. https://doi.org/10.1016/0957-4166(95)00236-I
  3. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823. https://doi.org/10.1016/S0040-4039(01)81300-9
  4. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. https://doi.org/10.1021/ja00279a083
  5. Noyori, R.; Suga, S.; Kawai, K.; Kitamura,M.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda,Y. J. Organomet. Chem. 1990, 382, 19. https://doi.org/10.1016/0022-328X(90)85212-H
  6. Iovel, I.; Oehme,G.; Lukevics, E. Appl. Organomet. Chem. 1998, 12, 469. https://doi.org/10.1002/(SICI)1099-0739(199807)12:7<469::AID-AOC739>3.0.CO;2-X
  7. Paleo,M. R.; Cabeza, I.; Sardina, F. J. J. Org. Chem. 2000, 65, 2108. https://doi.org/10.1021/jo9917083
  8. Nugent, W. A. Org. Lett. 2002, 4, 2133. https://doi.org/10.1021/ol0259488
  9. Jiang, B.; Chen, Z.;Xiong, W. Chem. Commun. 2002, 1524.
  10. Pizzuti, M. G.; Superchi,S. Tetrahedron: Asymmetry 2005, 16, 2263. https://doi.org/10.1016/j.tetasy.2005.05.028
  11. Jimeno, C.;Pasto, M.; Riera, A.; Pericas, M. A. J. Org. Chem. 2003, 68, 3130. https://doi.org/10.1021/jo034007l
  12. Yang, X. F.; Hirose, T.; Zhang, G. Y. Tetrahedron: Asymmetry2008, 19, 1670. https://doi.org/10.1016/j.tetasy.2008.06.027
  13. Scarpi, D.; Occhiato, E. G.; Guarna, A. Tetrahedron: Asymmetry 2009, 20, 340. https://doi.org/10.1016/j.tetasy.2009.01.021
  14. Dai, W. M.; Zhu, H. J.; Hao, X. J. Tetrahedron: Asymmetry1996, 7, 1245. https://doi.org/10.1016/0957-4166(96)00133-4
  15. Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997,62, 3770. https://doi.org/10.1021/jo970047b
  16. Kitamura, M.; Suga, S.; Miwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832. https://doi.org/10.1021/ja00122a013
  17. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. https://doi.org/10.1021/cr00013a004
  18. Kang, S. W.; Ko, D. H.; Kim, K. H.; Ha, D. C. Organic Lett.2003, 5, 4517. https://doi.org/10.1021/ol0358511
  19. Lin, G. Q.; Chen, Y. Q.; Chen, X. Z.; Li, Y. M. Chiral Synthesis: Asymmetric Reactions and Their Applications; Science Press: Beijing, 2000.
  20. Yun, H. Y.; Wu, Y. J.; Wu, Y. S.;Ding, K. L.; Zhou, Y. Tetrahedron Lett. 2000, 41, 10263. https://doi.org/10.1016/S0040-4039(00)01842-6
  21. Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757. https://doi.org/10.1021/cr000411y
  22. Hsieh, S. H.; Gau, H. M. Chirality 2006, 18, 569. https://doi.org/10.1002/chir.20279
  23. Unaleroglu, C.; Aydin, A. E.; Demir, A. S. Tetrahedron: Asymmetry 2007, 17, 742.
  24. Braga, A. L.; Galetto, F. Z.; Rodrigues, O. E. D.; Silveira, C. C.; Paixao, M.W. Chirality 2008, 20, 839. https://doi.org/10.1002/chir.20554
  25. Grach, G.; Reboul, V.; Metzner, P.Tetrahedron: Asymmetry 2008, 19, 1744. https://doi.org/10.1016/j.tetasy.2008.06.031
  26. Binder, C. M.; Bautista,A.; Zaidlewicz, M.; Krzemiski, M. P.; Oliver, A.; Singaram,B. J. Org. Chem. 2009, 74, 2337. https://doi.org/10.1021/jo802371z
  27. Wang, M. C.; Zhang, Q. J.; Li,G. W.; Liu, Z. K. Tetrahedron: Asymmetry 2009, 20, 288. https://doi.org/10.1016/j.tetasy.2008.12.032
  28. Wang, H. Z.; Wu, Y. R.; Yin, C. L. Journal of Beijing Normal University (Natural Science) 1997, 31, 96.
  29. He, Q.; Peng, Y. F.Fine Chemical Intermediates 2004, 35, 27.
  30. Wang, L. C.; Chen,H. M.; Huang, Z. Chinese Journal of Medicinal Chemistry 2003,13, 356.
  31. Schmidt, A. M.; Eilbracht, P. J. Org. Chem. 2005, 70, 5528. https://doi.org/10.1021/jo050464l
  32. Falorni, M.; Collu, C.; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 293. https://doi.org/10.1016/0957-4166(95)00448-3
  33. Huang, H. L.; Lin, Y. C.; Chen, S. F.;Wang, C. L.; Liu, L. T. Tetrahedron: Asymmetry 1996, 7, 3067. https://doi.org/10.1016/0957-4166(96)00399-0
  34. Tanaka, T.; Yasuda, Y.; Hayashi, M. J. Org. Chem. 2006, 71, 7091. https://doi.org/10.1021/jo060964u
  35. Prasad, K. R. K.; Joshi, N. N. Tetrahedron: Asymmetry 1997, 8, 173. https://doi.org/10.1016/S0957-4166(96)00514-9
  36. Kang, S. K.; Jeon, J. H.; Yamaguehi, T.; Kim, J. S.; Ko, B. S. Tetrahedron: Asymmetry 1995, 6, 2139. https://doi.org/10.1016/0957-4166(95)00284-V
  37. Butz, T.; Sauer, J. Tetrahedron: Asymmetry 1997, 8, 703. https://doi.org/10.1016/S0957-4166(97)00015-3

Cited by

  1. Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands vol.14, pp.47, 2016, https://doi.org/10.1039/C6OB01878E
  2. L-Alanine-derived Chiral Ligands for Asymmetric Addition of Diethylzinc to Aldehydes vol.33, pp.9, 2010, https://doi.org/10.5012/bkcs.2012.33.9.3125
  3. N-Trityl-aziridinyl alcohols as highly efficient chiral catalysts in asymmetric additions of organozinc species to aldehydes vol.26, pp.1, 2010, https://doi.org/10.1016/j.tetasy.2014.11.016
  4. Efficient Asymmetric Simmons-Smith Cyclopropanation and Diethylzinc Addition to Aldehydes Promoted by Enantiomeric Aziridine-Phosphines vol.11, pp.8, 2021, https://doi.org/10.3390/catal11080968