Studies on the Synthesis of Aryl Ethers Using Arene-Manganese Chemistry
Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described.The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schoellkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes.Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.
Pearson, Anthony J.,Bruhn, Paul R.
p. 7092 - 7097
(2007/10/02)
Stereoselective Synthesis of Arylglycine Derivatives using Arene-manganese Tricarbonyl Complexes
Arene-Mn(CO)3 cations react with the Schoellkopf chiral glycine enolate equivalent (1) or (2) to give dienyl-Mn(CO)3 complexes which are converted to arylglycine methyl esters; the reaction sequence can be performed on arene-Mn(CO)3 complexes having protected amino acid substituents to give diaryl ethers having amino ester groups on both aromatic rings.
Pearson, Anthony J.,Bruhn, Paul R.,Gouzoules, Fred,Lee, Seung-Han
p. 659 - 661
(2007/10/02)
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