期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 9, 页码 1942-1950出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301866
关键词
Domino reactions; Michael addition; Aldol reactions; Cyclopropenes
资金
- National Natural Science Foundation of China (NSFC) [21172082, 20872041]
A highly regioselective cascade formal nucleophilic substitution and aldol reaction of 2-aroyl-1-chlorocyclopropanecarboxylic esters with salicylic aldehydes is described. Under basic conditions, 2-aroyl-1-chlorocyclopropanecarboxylic esters are easily converted into cyclopropene intermediates by simple 1,2-elimination of hydrogen chloride. This highly reactive cyclopropene quickly combines with salicylic aldehyde through a regioselective oxa-addition to the strained C=C bond and a subsequent intramolecular aldol reaction to construct C-O and C-C bonds concomitantly and afford tetrahydrocyclopropa[b]chromene derivatives.
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