Organic Chemistry Portal

Abstracts

Search:

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

Abstract

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



Key Words

MOM Ethers, Silyl Ethers, Cleavage of Acetals


ID: J54-Y2009-3350