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Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases

Nikos Assimomytis, Yiannis Sariyannis, Georgios Stavropoulos, Petros G. Tsoungas*, George Varvounis, Paul Cordopatis

*Department of Research and Technology, Ministry of Development, 14-18 Messogion Ave., 11510 Athens, Greece, Email: pgtgsrt.gr

N. Assimomytis, Y. Sariyannis, G. Stavropoulos, P. G. Tsoungas, G. Varvounis, P. Cordopatis, Synlett, 2009, 2777-2782.

DOI: 10.1055/s-0029-1217991 (free Supporting Information)


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Abstract

Phenol carbamates undergo an anionic ortho-Fries rearrangement to their corresponding amides in the presence of LDA. Sterically hindered substrates can be converted with s-BuLi/TMEDA at -90C. The amides can be efficiently reduced with lithium aluminum hydride to the corresponding Mannich bases.

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Key Words

rearrangements, ortho-Fries rearrangement, directed ortho metalation, reduction of amides, Mannich bases, carbamates, lithium aluminum hydride


ID: J60-Y2009-2940