Citation:
Zhen Zhang, Kai Yang, Qiuling Song. Introduction to the Stereoselective Synthesis of Oximes[J]. University Chemistry,
;2024, 39(1): 105-110.
doi:
10.3866/PKU.DXHX202306022
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Stereoselectively pure oximes play a pivotal role in organic synthesis, pharmaceuticals, and as food additives. Traditional synthesis methods rely heavily on the steric hindrance of substrate substituents to achieve oxime stereoselectivity, presenting a significant challenge in organic synthesis. This article offers a concise overview of the latest advancements in techniques and methods for stereoselective oxime synthesis. The insights presented herein are rooted in fundamental organic chemistry. Introducing these concepts into academic curriculum can broaden student perspectives and ignite their enthusiasm for problem discovery and resolution.
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-
[1]
-
[2]
-
[3]
-
[4]
Politzer, P.; Murray, J. The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids; Rappoport, Z., Liebman, J. F. Eds.; John Wiley & Sons, Ltd.: Hoboken, USA, 2008; pp. 29–51.
-
[5]
Donaruma, L. G.; Heldt, W. Z. Org. React. 1960, 11, 1.
-
[6]
Palani, A.; Shapiro, S.; Josien, H.; Bara, T.; Clader, J. W.; Greenlee, W. J.; Cox, K.; Strizki, J. M.; Baroudy, B. M. J. Med. Chem. 2002, 45, 3143.
-
[7]
Bolotin, D. S.; Bokach, N. A.; Demakova, M. Y.; Kukushkin, V. Y. Chem. Rev. 2017, 117, 13039.
-
[8]
-
[9]
Smith, J. H.; Kaiser, E. T. J. Org. Chem. 1974, 39, 728.
-
[10]
Dolliver, D. D.; Bhattarai, B. T.; Pandey, A.; Lanier, M. L.; Bordelon, A. S.; Adhikari, S.; Dinser, J. A.; Flowers, P. F.; Wills, V. S.; Schneider, C. L.; et al. J. Org. Chem. 2013, 78, 3676.
-
[11]
Yang, K.; Zhang, F.; Fang, T.; Zhang, G.; Song, Q. Angew. Chem. Int. Ed. 2019, 58, 13421.
-
[12]
Padwa, A.; Albrecht, F. J. Am. Chem. Soc. 1972, 94, 1000.
-
[13]
Yuan, P.-F.; Huang, T.; He, J.; Huang, X.-T.; Jin, X.-L.; Sun, C.; Wu, L.-Z.; Liu, Q. Org. Chem. Front. 2021, 8, 5785.
-
[14]
Zhang, X.; Rovis, T. J. Am. Chem. Soc. 2021, 143, 21211.
-
[15]
Li, Y.; Zhang, D.; Ye, J.; Mai, Y.; Wang, C.; Yang, Y.; Li, Y.; Besenbacher, F.; Niemantsverdriet, H.; Rosei, F.; et al. Angew. Chem. Int. Ed. 2023, 62, e202302979.
-
[1]
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