期刊
TETRAHEDRON LETTERS
卷 58, 期 38, 页码 3712-3716出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.08.025
关键词
Donor-acceptor cyclopropanes; Aromatic aldehydes 1,2-Zwitterion; Gallium trichloride; Dioxabicydo[3.3.0]octan-2-ones
资金
- Russian Science Foundation [14-13-01054-P]
- Russian Science Foundation [17-13-00080] Funding Source: Russian Science Foundation
A new reaction of 2-arylcyclopropane-1,1-dicarboxylates (ACDC) with aromatic aldehydes that occurs via generation of a 1,2-zwitterionic intermediate in the presence of GaCl3 has been developed. This process results in the 3,7-dioxabicyclo[3.3.0]octane frame by addition of two aldehyde molecules to an ACDC molecule. The reaction is a complex anionic-cationic cascade process involving the formation of two C-C bonds, two C-O bonds, and five stereocenters. The process occurs with high diastereoselectivity to give only one diastereomer. A probable reaction mechanism is suggested and confirmed by NMR monitoring data. (C) 2017 Elsevier Ltd. All rights reserved.
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