Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

• DOI: 10.1021/acs.orglett.7b01556
• Publication Date: 2017-06-29T15:21:07Z
• Authors: Denis D. Borisov; Roman A. Novikov; Anna S. Eltysheva; Yaroslav V. Tkachev; Yury V. Tomilov
• Keywords: Dihydropyran; Acceptor

A new strategy for modifying the reactivity of donor–acceptor cyclopropanes (DAC) has been suggested. It involves use isomeric styrylmalonates as alternative sources reactive intermediates. The efficiency approach demonstrated in reactions with aromatic aldehydes. As a result, process construction 5,6-dihydropyran-2-one skeleton developed. efficiently occurs high diastereoselectivity presence BF3·Et2O; products can be easily isolated by crystallization. subsequent resulting dihydropyranones syntheses providing convenient access to various classes compounds broad molecular diversity demonstrated.