Excellent Preparation of Azetidin-3-Ones from Propargylic Alcohols by Gold-Catalysis

Article Preview

Abstract:

Azetidin-3-ones are important heterocycles in organic synthesis and pharmaceutical chemistry. With gold-catalyzed alkyne intermolecular oxidation, these versatile heterocycles can be prepared in three steps from readily available propargylic alcohols with high efficiencies.

You might also be interested in these eBooks

Info:

Periodical:

Advanced Materials Research (Volumes 634-638)

Pages:

970-974

Citation:

Online since:

January 2013

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2013 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

[1] For a recent review, see: (a) Kobayashi, J. i.; Cheng, J. -F.; Ishibashi, M.; Walchli, M. R.; Yamamura, S.; Ohizumi, Y. J. Chem. Soc., Perkin Trans. 1991, 1, 135; (b) Ohshita, K.; Ishiyama, H.; Takahashi, Y.; Ito, J.; Mikami, Y.; Kobayashi, J. i. Biorg. Med. Chem. 2007, 15, 4910.

Google Scholar

[2] Alvi, K. A.; Jaspars, M.; Crews, P.; Strulovici, B.; Oto, E. Biorg. Med. Chem. Lett. 1994, 4, 2447.

Google Scholar

[3] For a recent review, see: (a) Suzuki, S.; Isono, K.; Nagatsu, J.; Mizutani, T.; Kawashima, Y.; Mizuno, T. J. Antibiot. 1965, 131; (b) Isono, K.; Nagatsu, J.; Kawashima, Y.; Suzuki, S. Agri. Biol. Chem. 1965, 29, 848.

DOI: 10.1271/bbb1961.29.848

Google Scholar

[4] For a recent review, see: (a) Privitera, M.; Treiman, D.; Pledger, G.; Sahlroot, J.; Handforth, A.; Linde, M.; France, C.; Cereghino, J.; McCutchen, C.; Wood, J. Neurology 1994, 44, 1453; (b) Johnson, D. N.; Osman, M. A.; Cheng, L. K.; Swinyard, E. A. Epilepsy Res. 1990, 5, 185.

DOI: 10.1212/wnl.44.8.1453

Google Scholar

[5] Yagil Y, M. M., Frasier L, Oizumi K, Koike H. Am. J. Hypertens. 1994, 637.

Google Scholar

[6] Isoda, T.; Yamamura, I.; Tamai, S.; Kumagai, T.; Nagao, Y. Chem. Pharm. Bull. 2006, 54, 1408.

Google Scholar

[7] For a recent review, see: (a) Gerhard, E. Tetrahedron 1992, 48, 7165; (b) Hanessian, S.; Fu, J. -M.; Chiara, J. -L.; Fabio, R. D. Tetrahedron Lett. 1993, 34, 4157.

Google Scholar

[8] For a recent review, see: (a) Seo, G.; Akimoto, Y.; Hamashima, H.; Masuda, K.; Shiojima, K.; Sakuma, C.; Sasatsu, M.; Arai, T. Microbios 2000, 101, 105; (b) Ozone, F.; Inoue, Y.; Shiraishi, A.; Hamashima, H.; Masuda, K.; Shiojima, K.; Sasatsu, M. J. Microbiol. Methods 2002, 50, 91.

DOI: 10.1016/s0167-7012(02)00022-2

Google Scholar

[9] For a recent review, see: (a) Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P. R. J. Org. Chem. 1995, 60, 1959; (b) Katritzky, A. R.; Cundy, D. J.; Chen, J. J. Heterocycl. Chem. 1994, 31, 271.

Google Scholar

[10] For a recent review, see: (a) Burkhard, J. A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. M. Angew. Chem. Int. Ed. 2010, 49, 3524; (b) Burkhard, J. A.; Guérot, C.; Knust, H.; Rogers-Evans, M.; Carreira, E. M. Org. Lett. 2010, 12, (1944).

DOI: 10.1002/anie.200907108

Google Scholar

[11] Dejaegher, Y.; Kuz'menok, N. M.; Zvonok, A. M.; De Kimpe, N. Chem. Rev. 2002, 102, 29.

Google Scholar

[12] For selected recent reviews, see: (a) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271; (b) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.

Google Scholar

[13] Ye, L.; He, W.; Zhang, L. Angew. Chem. Int. Ed. 2011, 50, 3236.

Google Scholar

[14] For a recent review, see: (a) Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226; (b)Bhunia, S.; Ghorpade, S.; Huple, D. B.; Liu, R. -S. Angew. Chem. Int. Ed. 2012, 51, 2939; (c) Gronnier, C.; Kramer, S; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2012, 134, 828; (d) Wang, Y.; Ji, K.; Lan, S.; Zhang, L. Angew. Chem. Int. Ed. 2012, 51, (1915).

DOI: 10.1002/anie.201290080

Google Scholar

[15] Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, (1999).

Google Scholar

[16] Cost anasysis of protect group: chiral t-Bus($ 67. 40/g), raecmic t-Bus ($ 42. 60/g), N-Boc-toluenesulfonamide($ 7. 54/g) from Sigma-Aldrich.

Google Scholar

[17] Kavanagh, Y.; Chaney, C. a. M.; Muldoon, J.; Evans, P. J. Org. Chem. 2008, 73, 8601.

Google Scholar

[18] He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 133, 8482.

Google Scholar

[19] He, W.; Xie, L.; Xu, Y.; Xiang, J.; Zhang, L. Org. Biomol. Chem. 2012, 10, 3168.

Google Scholar

[20] Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258.

Google Scholar