Ciufolini, Marco A.2009-06-042009-06-041990Spencer, George Otis, III. "Studies towards the synthesis of complex 1,2 amino alcohols." (1990) Master’s Thesis, Rice University. <a href="https://hdl.handle.net/1911/13473">https://hdl.handle.net/1911/13473</a>.https://hdl.handle.net/1911/13473A 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.271 p.application/pdfengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.Organic chemistryThesisThesis Chem. 1990 Spencer