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The Formation of Cyclopropane Derivatives Bearing 1,2‐Dicarbonyl Groups through Tandem Michael–Favorskii‐Type Reactions with( E )‐β‐Styrylselenonium Triflate
Author(s) -
Watanabe Shinichi,
Nakayama Ippei,
Kataoka Tadashi
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400756
Subject(s) - carbanion , cyclopropane , chemistry , trifluoromethanesulfonate , methylene , michael reaction , tandem , medicinal chemistry , organic chemistry , stereochemistry , ring (chemistry) , catalysis , materials science , composite material
A novel tandem Michael–Favorskii‐type reaction is described. Treatment of active methylene carbanions, prepared by the reaction of NaH and active methylene compounds, with ( E )‐β‐styrylselenonium triflate in DMF at 70 °C for 3 h gave cyclopropane derivatives bearing 1,2‐dicarbonyl groups in moderate to good yields. On the other hand, the carbanions derived from malonates reacted with the selenonium salt to afford 1,1‐dicarbonylcyclopropane compounds in good yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)