Mild deprotection of methylene acetals in combination with trimethylsilyl triflate-2,2'-bipyridyl.
The facile deprotection of methylene acetal protection of diols under mild conditions is established. The combination of trimethylsilyl triflate (TMSOTf) and 2,2'-bipyridyl followed by a weakly acidic hydrolysis was effective and the substrates having acid sensitive functional groups can be tolerated under the stated conditions. The selective deprotection between methylene acetal and benzophenone ketal was achieved.
Fujioka
Hiromichi
H
Graduate School of Pharmaceutical Sciences, Osaka University, Osaka 565-0871, Japan. fujioka@phs.osaka-u.ac.jp
Senami
Kento
K
Kubo
Ozora
O
Yahata
Kenzo
K
Minamitsuji
Yutaka
Y
Maegawa
Tomohiro
T
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000737:chemistry; D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000080:Acetals; D000438:Alcohols; D014297:Trimethylsilyl Compounds; C549749:trimethylsilyl triflate-2,2'-bipyridyl; D015082:2,2'-Dipyridyl