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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1355-1361
Published online, 16th August, 2011
DOI: 10.3987/COM-11-S(P)77
Deprotection of 3,4-Dimethoxybenzyl (3,4DMB) Group on γ-Lactam Nitrogen Using Phenyliodine(III) Bis(trifluoroacetate) (PIFA): Application to Isoindolinone Compounds

Kazuhiro Watanabe, Hiroaki Shibata, Yū Imai, and Tadashi Katoh*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


The secondary amide (γ-lactam) moiety of an isoindolinone ring exhibits high polarity in an unprotected condition. Problems with solubility make handling difficult; therefore, introduction of a protective group is necessary. We discovered that the 3,4-dimethoxybenzyl (3,4DMB) group is an optimal protective group, and that the 3,4DMB group alone could be deprotected under mild conditions with the use of a hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA).