Tetrahedron

The reaction of acetal-type protective groups in combination with TMSOTf and 2, 2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other …

…, Y Minamitsuji, O Kubo, K Senami, T Maegawa

Index: Fujioka, Hiromichi; Minamitsuji, Yutaka; Kubo, Ozora; Senami, Kento; Maegawa, Tomohiro Tetrahedron, 2011 , vol. 67, # 16 p. 2949 - 2960

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Citation Number: 13

Abstract

A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2, 2′-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild ( ...

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