A range of N-H alkynylaziridines were prepared from amphoteric unprotected aziridine aldehydes without protecting-group manipulation. Unprotected alpha -amino allenes can be obtained from these strained propargyl amines via a 9-BBN mediated hydride transfer. Further transformation of alpha -amino allenes to 2,4,6-trisubstituted pyridines was realized. We also developed another class of amphoteric molecules – alpha-boryl aldehydes, equipped with the tetrahedral MIDA boryl group. A wide range of boryl-substituted building blocks or functionalized boronic acid derivatives have been accessed from these bench-stable alpha-borylcarbonyl compounds. Further chemoselective transformations of these alpha-boryl aldehyde
derived building blocks have been conducted, where alph-boryl isocyanates, alpha-aminoboronic acids, acylboronates, and borylated heterocycles were achieved through the decarboxylative functionalization of alpha-borylcarboxylic acids.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/34051 |
| Date | 13 December 2012 |
| Creators | He, Zhi |
| Contributors | Yudin, Andrei |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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