Synthesis and Structural Investigation of Internally Coordinated Alpha-Aminoboronic Acids

• 作 者: JackLai;
• 机 构: Department of Chemistry, University of Tufits, USA
• 出 处: 2005 WHTS'3rd Annual Congress of International Drug Disc
• 发表日期: 2005年期

　　A series of N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogs, have been synthesized by modification of conventional procedures.Structural characterization of these alpha-aminoboronic acids was accomplished by extensive use of 11B and 1H NMR spectroscopy.These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a 5-membered (:O=C-N-C-B) ring motif.It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms.Computational evidence from second-order Mler-Plesset perturbation theory is provided in support of these findings.