Studies towards the synthesis of complex 1,2 amino alcohols
Spencer, George Otis, III
Ciufolini, Marco A.
Master of Arts
A novel method for the synthesis of complex 1,2 amino alcohols of syn stereochemistry has been achieved via the condensation of $\gamma$-oxygenated allylstannanes with activated imines. The imines are activated by an N-aryl group, and boron trifluoride etherate. The N-aryl functionality serves to delocalize the negative charge developing on nitrogen. Imines with both N-aryl/C-aryl and N-aryl/C-aliphatic functionality have been prepared, and condensed with various allylstannanes. Previously unknown N-aryl/C-aliphatic imines have been synthesized for the first time, using a modified Wadsworth-Emmons reaction. The syn stereochemistry of the reaction has been proven by NOEDS of the oxazolone derivatives of the condensation products. The 4-carbomethoxyphenyl (4-CMP) group has been developed as an excellent activating group for the imine. The facile removal of this functionality has been demonstrated by use of the Birch reduction.