32346-57-9Relevant articles and documents
One-pot regio- and stereoselective cyclization of 1,2,n-triols
Zheng, Tao,Narayan, Radha S.,Schomaker, Jennifer M.,Borhan, Babak
, p. 6946 - 6947 (2007/10/03)
A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright
Base-induced rearrangement of oxiranylsilacylobutane into silacyclopentane. Application to stereoselective synthesis of 4-alken-1-ol and 1,4,5-triol
Matsumoto,Takeyama,Oshima,Utimoto
, p. 4545 - 4548 (2007/10/02)
Treatment of 1-methyl-1-(cis-1,2-epoxyhexyl)-1-silacyclobutane 16a with i-PrOLi provided erythro-1-methyl-1-isopropoxy-2-(2-hydroxypentyl)-1-silacyclopentane 17a which was converted into (Z)-4-nonen-1-ol 18, (E)-4-nonen-1-ol 19, or 1,4,5-nonanetriol 20, r
