273221-16-2

Upstream product

• 62411-81-8 3-methyl-2-[4-(methyloxy)phenyl]-2-cyclopenten-1-one 
• 273221-14-0 (1R)-3-methyl-2-[4-(methyloxy)phenyl]cyclopent-2-en-1-ol 
• 273221-15-1 (1R,2R,5S)-5-methyl-1-[4-(methyloxy)phenyl]-6-oxabicyclo[3.1.0]hexane-2-ol 
• 62-23-7 4-nitro-benzoic acid 

Relevant academic research and scientific papers

Study of the Lewis acid-promoted rearrangement of 2-aryl-2,3-epoxy acylates

The reaction of 2-aryl-2,3-epoxy acylates with Lewis acids was examined in detail. Cyclic 2-aryl-2,3-epoxy acylates afforded the rearranged products via C2-carbocation intermediates. On the other hand, acyclic ones gave the rearranged products via phenonium ion intermediates obtained by C3-cleavage of oxirane rings. The method was also applied to the synthesis of the optically active benzylic quaternary carbon center.

Acid-promoted rearrangement of 2-aryl-2,3-epoxy acylates: Construction of chiral benzylic quaternary carbon centers

The reactions of 2-aryl-2,3-epoxy acylates with BF3·Et2O were examined in detail. Trans-2-aryl-2,3-epoxy acylates afforded the rearranged products in good yields via the C2-carbocation intermediates. The reaction was used for constructing the optically active benzylic quaternary carbon center. (C) 2000 Elsevier Science Ltd.