effect of substituents
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Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7386
Author(s):  
Carlos Díez-Poza ◽  
Asunción Barbero

The regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The 5-exo opening being preferred vs. the 6-endo mode, according to Baldwin rules, the use of silyl-substituted oxiranes has been reported as a possible method to favor the 6-endo cyclization. However, there is a need for a detailed study on the different factors (structural factors, catalyst nature or conditions) that influence this process. In this paper, the acid-catalyzed cyclization of epoxysilyl alcohols was studied, focusing on the effect of substituents and reaction conditions on the outcome of the process. Two types of heterocycles (tetrahydrofurans or tetrahydropyrans) were selectively obtained depending on the structure of the initial epoxysilyl alcohol. Interestingly, cyclization of hindered epoxysilyl alcohols mainly proceeds through an unexpected side reaction, which implies a previous isomerization to an aldehyde. A mechanistic proposal for the formation of the different products is presented.


2021 ◽  
Vol 70 (8) ◽  
pp. 1533-1536
Author(s):  
S. E. Lyubimov ◽  
A. A. Zvinchuk ◽  
R. R. Aysin ◽  
B. Chowdhury

ChemistryOpen ◽  
2021 ◽  
Vol 10 (8) ◽  
pp. 852-859
Author(s):  
Karuppasamy Ganesh ◽  
Jaewon Jung ◽  
Jun Woo Park ◽  
Byeong‐Su Kim ◽  
Sungbaek Seo

Author(s):  
Rafael Muñoz-Mármol ◽  
Pedro G. Boj ◽  
José M. Villalvilla ◽  
José A. Quintana ◽  
Nathalie Zink-Lorre ◽  
...  

2021 ◽  
Vol 140 (5) ◽  
Author(s):  
Huimin Kang ◽  
Jinting Ye ◽  
Hongqiang Wang ◽  
Yuan Zhang ◽  
Yongqing Qiu

2021 ◽  
pp. 109470
Author(s):  
Inês F.A. Mariz ◽  
Sebastian Raja ◽  
Tiago Silva ◽  
Suzete Almeida ◽  
Érica Torres ◽  
...  

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