- One-Pot, Pd-catalyzed synthesis of trans -dihydrobenzofurans from o -aminophenols
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Figure presented An efficient and facile synthesis of trans- dihydrobenzofurans has been accomplished from o-aminophenols and phenylpropenes via a novel (one-pot) diastereoselective Pd-catalyzed oxyarylation reaction. The development and optimization of this method is described.
- Coy B., Ericsson D.,Jovanovic, Ljubisa,Sefkow, Michael
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supporting information; scheme or table
p. 1976 - 1979
(2010/07/06)
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- Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles
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(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [Ru II(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D 4-Por*)(CO)] as catalyst, and up to 96% ee is attained.
- Cheung, Wai-Hung,Zheng, Shi-Long,Yu, Wing-Yiu,Zhou, Guo-Chuan,Che, Chi-Ming
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p. 2535 - 2538
(2007/10/03)
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- Synthesis of 2,3-dihydrobenzofurans by Mn(OAc)3-based oxidative cycloaddition of 2-cyclohexenones with alkenes. Synthesis of (±)-conocarpan
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Oxidative cycloaddition of a 2-cyclohexenone or α-tetralone and an alkene with dried Mn(OAc)3 in benzene at 80-140 °C provides a general route to dihydrobenzofurans 15 and dihydronaphthofurans 17. Although the yields are modest, this one-pot reaction provides simple access to these compounds, which have previously been prepared by multistep routes. Oxidative cycloaddition of 2-cyclohexenones with β-methylstyrenes provides a new route to benzofuranoid neolignans, which was applied to the synthesis of conocarpan (22). The formation of 2-acetoxyhexanedioic acids 27 and 47 from acetoxylation of 2-cyclohexenones in HOAc, but not in benzene, opens up a new class of Mn(OAc)3 reactions and explains Watt and Demir's discovery that much higher yields of α'-acetoxy enones are obtained in benzene than in HOAc.
- Snider, Barry B.,Han, Luning,Xie, Chaoyu
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p. 6978 - 6984
(2007/10/03)
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