Synthesis of silyloxyacrolein for [4+3] cycloaddition and preparation of carbonate closomer

Abstract

[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT AUTHOR'S REQUEST.] Followed by Funk's method, I synthesized silyloxyacroleins and used them as dienophiles to react with different dienes in [4+3] cycloaddition reaction. These enals such as 2-(tert-butyldimethylsilyloxy)-hept-2-eanl can undergo [4 + 3] cyclizations with different dienes in the presence of Lewis acids or Brønsted acid with excellent regio- and stereoselectivity. The reaction conditions for the synthesis dodecacarbonate-closo-dodecaborate were optimized. This carbonate closomer can be used in a drug delivery system. The stability of this dodecacarbonate-closo-dodecaborate was examined: it is stable in acid environment, but can be decomposed into 4-nitrophenol gradually in basic solutions. The solubility of this carbonate closomer was also investigated: it does not dissolve in water, but has a good solubility in diethyl ether and toluene.