Tetrahedron

Factors affecting orthogonality in the deprotection of 2, 4-di-protected aromatic ethers employing solid-supported acids

K Tangdenpaisal, S Sualek, S Ruchirawat…

文献索引：Tangdenpaisal, Kassrin; Sualek, Supannee; Ruchirawat, Somsak; Ploypradith, Poonsakdi Tetrahedron, 2009 , vol. 65, # 22 p. 4316 - 4325

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被引用次数: 23

摘要

Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was systematically investigated. ortho-Directing protonation by the carbonyl group as well as carbocation stability and quenching are the important determining factors for the orthogonal deprotection process. Stablilized carbocations (eg, those from the MOM and PMB groups) could be ...