3343-45-1Relevant articles and documents
Reactions of cephalosporin sulphones 1. Rearrangement of the β-lactam ring to a triazole derivative
Gunda, Tamas E.,Tamas, Laszlo,Salyi, Szabolcs
, p. 3061 - 3064 (1998)
The 7β-amino-cephalosporin sulphones, generated in situ from the appropriate 7β-tBoc-amino derivative and diazotized in a one-pot reaction in aq. HClO4 - MeOH - NaNO2, rearrange exclusively to the triazoles 5 in a multistep reaction.
Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
Li, Ling,Zhang, Shiqi,Deng, Xiongfei,Li, Guangxun,Tang, Zhuo,Zhao, Gang
, p. 6819 - 6824 (2021/09/08)
α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.
One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones
Wang, Lei,Song, Wei,Wang, Binju,Zhang, Yan,Xu, Xin,Wu, Jing,Gao, Cong,Liu, Jia,Chen, Xiulai,Chen, Jinghua,Liu, Liming
, p. 2808 - 2818 (2021/03/15)
2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.
