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Lewis acid catalyzed reactions of methylenecyclopropylcarbinols with acetals for the construction of 3-oxabicyclo[3.1.0]hexane derivatives |
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| Authors: | Li-Xiong Shao Min Shi |
| Institution: | a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China b College of Chemistry and Materials Engineering, Wenzhou University, Chashan University Town, Wenzhou, Zhejiang Province 325035, PR China |
| Abstract: | Reactions of methylenecyclopropylcarbinols 1 with acetals 2 in the presence of Lewis acid Sc(OPf)3 produce the ring-closure products 3-oxabicyclo3.1.0]hexane in moderate to high total yields along with the products in trans-configuration as the sole or major one. The plausible reaction mechanism has been discussed, which is based on the Prins-type reaction mechanism. |
| Keywords: | Lewis acid Methylenecyclopropylcarbinols Acetals Prins-type reaction 3-Oxobicyclo[3 1 0]hexane |
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