Novel Regiocontrolled Protection of 1,2- and 1,3-Diols via Mild Cleavage of Methylene Acetals
Hiromichi Fujioka*, Kento Senami, Ozora Kubo, Kenzo Yahata, Yutaka Minamitsuji and Tomohiro Maegawa
*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka Suita, Osaka 565-0871, Japan, Email: fujiokaphs.osaka-u.ac.jp
H. Fujioka, K. Senami, O. Kubo, K. Yahata, Y. Minamitsuji, T. Maegawa, Org. Lett., 2009, 11, 5138-5141.
DOI: 10.1021/ol902088b (free Supporting Information)
see article for more reactions
Different types of unsymmetrically protected diols are available from the methylene acetal in a one-pot procedure. Monoprotected 1,2-diols with a silyl group at the less hindered hydroxy group as well as with a MOM group at the more hindered can be isolated in good yields. The reaction conditions are mild without affecting other functional groups.
see article for more examples