Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/151876
Title: SYNTHESIS OF N-HETEROCYCLES WITH ACTIVATED ISOCYANIDES
Authors: GERMAINE KOK PUI YANN
Keywords: isocyanoacetates, cycloaddition, pyrroles, tetrahydropyrimidine, catalysis, methodology
Issue Date: 3-Aug-2018
Citation: GERMAINE KOK PUI YANN (2018-08-03). SYNTHESIS OF N-HETEROCYCLES WITH ACTIVATED ISOCYANIDES. ScholarBank@NUS Repository.
Abstract: The development of efficient and stereoselective synthesis of heterocycles is a focal objective in organic chemistry. Isocyanoacetates have served as efficient building blocks of N-heterocycles due to the immense potential of its versatile functionality. These compounds can undergo cycloaddition with various π-systems such as carbonyls, imines, α,β-unsaturated carbonyls or activated alkenes/alkynes to produce a variety of N-heterocycles. In this dissertation, we have developed an efficient Cu-catalyzed formal [3+3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In particular, the use of enantiopure aziridines delivers disubstituted tetrahydropyrimidines bearing a 1,3-diamino unit in good yields as a single stereoisomer. These products can also be easily converted to synthetically useful amino alcohol derivatives or α,γ-diamino acids. In addition, the divergent, enantioselective synthesis of 1H-pyrroles, 3H-pyrroles and bicyclic imidazolines through unprecedented [3+2] cycloaddition of allenoates with isocyanoacetates has also been achieved under silver or phosphine catalysis.
URI: http://scholarbank.nus.edu.sg/handle/10635/151876
Appears in Collections:Ph.D Theses (Open)

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