Novel regiocontrolled protection of 1,2- and 1,3-diols via mild cleavage of methylene acetals.
The regiocontrolled protection of unsymmetrical 1,2- and 1,3-diols has been developed. Different types of protected diols are available from the methylene acetal in a one-pot procedure. Highly regioselective protection of diols with a silyl group at the less hindered hydroxy group as well as with a MOM group at the more hindered one were achieved. The reaction conditions are mild without affecting other functional groups including acid-labile function.
Fujioka
Hiromichi
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka Suita, 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
D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000080:Acetals; D000438:Alcohols