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Metal-free, PTSA catalyzed facile synthesis of β-ketoacetal from β-chlorocinnamaldehyde
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2018-07-07 , DOI: 10.1016/j.tetlet.2018.07.022
Avinash K. Srivastava , Munsaf Ali , Kamal Nayan Sharma , Raj K. Joshi

A toluene solution of β-chlorocinnamaldehyde and dihydroxy alcohols in the catalytic presence of para-toluenesulphonic acid (PTSA) yield the β-ketoacetal in good to outstanding amount. The catalyst (PTSA), first selectively protect the aldehydic group to form the β-chloroacetal and the subsequent dechlorination by H2O result the β-ketoacetal. Significant transformation was achieved with electron donating substituent attached at the para-position of cinnamaldehyde. The selective formation of β-keto-1,3-acetal was also obtained with a mixture of 1, 2- and 1, 3- diol. The present reaction consists of a metal-free, economical, robustly feasible, sizeable functional group tolerance and high yield properties. Moreover, the use of different dihydroxy alcohols made this process more benign and valuable towards the metal-free development of ketones. First, of its kind, a rare and unusual multitasking nature of PTSA is observed.



中文翻译:

无金属,PTSA催化从β-氯肉桂醛轻松合成β-酮缩醛

甲苯磺酸(PTSA)的催化存在下,β-氯肉桂醛和二羟基醇的甲苯溶液可产生良好至显着量的β-酮缩醛。催化剂(PTSA)首先选择性地保护醛基以形成β-氯缩醛,随后通过H 2 O脱氯得到β-酮缩醛。通过在对连接的供电子取代基实现了显着的转化肉桂醛的位置。还用1、2-和1,3-二醇的混合物选择性地形成了β-酮-1,3-缩醛。本反应由无金属的,经济的,鲁棒可行的,可观的官能团耐受性和高产率性质组成。而且,使用不同的二羟基醇使该方法对酮的无金属开发更加有益和有价值。首先,观察到PTSA罕见且不寻常的多任务性质。

更新日期:2018-07-07
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