132203-97-5Relevant academic research and scientific papers
Efficient and highly selective cyclization induced by Lewis acid to generate 2-hydroxyl-α-cyclogeraniol
Wang, Zi,Qi, Weiyi,Yan, Yixuan,Hu, Youhong,Song, Linhua
supporting information, p. 1932 - 1939 (2016/11/25)
A cyclization reaction of the hydroxyl-protected geraniol epoxide induced by the different Lewis acids to generate 2-hydroxyl-α-cyclogeraniol has been explored. Compared with the previous methods, this method enhances the production and selectivity of this reaction without the consumption of a large amount of solvent. Also, the coordination of the metal with two oxygen atoms of hydroxyl groups might be crucial for the reaction is first addressed.
Acid-catalyzed cyclization of terpenes under homogeneous and heterogeneous conditions as probed through stereoisotopic studies: A concerted process with competing preorganized chair and boat transition states
Raptis, Christos,Lykakis, Ioannis N.,Tsangarakis, Constantinos,Stratakis, Manolis
scheme or table, p. 11918 - 11927 (2010/04/28)
Based on stereoisotopic studies and β-secondary isotope effects, we propose that the acid-catalyzed cyclization of geranyl acetate proceeds through a concerted mechanism. Under heterogeneous conditions (zeolite Y confinement), a preorganized chairlike transition state predominates, whereas under homogeneous conditions the boat-and chairlike transition states are almost isoenergetic. For the case of farnesyl acetate, we propose that under homogeneous conditions a concerted dicyclization occurs with a preorganized boat-chair transition state competing with the chair-chair transition state. Under zeolite confinement conditions, the chair-chairlike dicyclization transition state is highly favorable. The preference of chairlike transition states within the cavities of zeolite Y is attributed to a transition state shape selectivity effect.
