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Synthesis of N -Heterocycles - Organic Chemistry Portal

This thesis describes the development of new methods for the synthesis of 1,2-
diamines. Chapter one reviews current methods for the synthesis of 1,2-
diamines, and their importance in chemistry. Chapter two highlights attempts to
synthesise 1,2-diamines using two nitrogen-containing heterocycles, namely 3-
phenyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione and imidazolin-2-one,
which both contain an endocyclic double bond. It includes the synthesis of a
novel 1,2-diazetine as well as the functionalisation of imidazolin-2-one via a
palladium-catalysed cross-coupling reaction with phenyl iodide. Subsequent
hydrogenation and hydrolysis was then utilised to afford 1-phenylethane-1,2-
diamine dihydrochloride. Chapter three describes the synthesis and
functionalisation of a range of 3-methylene-1,2-diazetidines that were
subsequently hydrogenated in an asymmetric fashion, with [Rh(NBD)2]BF4 and
ligand Mandyphos M004-1, to yield 1,2-diazetidines with up to 89% ee.
Reduction with LiDBB allowed for the synthesis of two carbamate-protected
1,2-diamines in three steps. The first examples of epoxidation, reaction with
tetracyanoethylene and 1,3-dipolar cycloadditions of 3-methylene-1,2-
diazetidines are reported. Chapter four details the experimental procedures and
characterisation data for the novel compounds produced.

1,2-Amino Alcohols and Their Heterocyclic Derivatives …

This thesis describes the development of new methods for the synthesis of 1,2-
diamines. Chapter one reviews current methods for the synthesis of 1,2-
diamines, and their importance in chemistry. Chapter two highlights attempts to
synthesise 1,2-diamines using two nitrogen-containing heterocycles, namely 3-
phenyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione and imidazolin-2-one,
which both contain an endocyclic double bond. It includes the synthesis of a
novel 1,2-diazetine as well as the functionalisation of imidazolin-2-one via a
palladium-catalysed cross-coupling reaction with phenyl iodide. Subsequent
hydrogenation and hydrolysis was then utilised to afford 1-phenylethane-1,2-
diamine dihydrochloride. Chapter three describes the synthesis and
functionalisation of a range of 3-methylene-1,2-diazetidines that were
subsequently hydrogenated in an asymmetric fashion, with [Rh(NBD)2]BF4 and
ligand Mandyphos M004-1, to yield 1,2-diazetidines with up to 89% ee.
Reduction with LiDBB allowed for the synthesis of two carbamate-protected
1,2-diamines in three steps. The first examples of epoxidation, reaction with
tetracyanoethylene and 1,3-dipolar cycloadditions of 3-methylene-1,2-
diazetidines are reported. Chapter four details the experimental procedures and
characterisation data for the novel compounds produced.

Rhodium-Catalyzed Asymmetric 1,4-Addition and Its …

The development of new methods for the efficient synthesis of aziridines has been of considerable interest to researchers for more than 60 years, but no single method has yet emerged as uniformly applicable, especially for asymmetric synthesis of chiral aziridines. One method which has been intensely examined and expanded of late involves the nucleophilic addition to imines by anions bearing a-leaving groups; by analogy with the glycidate epoxide synthesis, these processes are often described as "aza-Darzens reactions". This Microreview gives a summary of the area, with a focus on contemporary developments. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

His research interests are focused in the chemistry of polyphenolic and nitrogen heterocyclic compounds, with special emphasis on the development of new synthetic routes and also on organocatalytic and metal-catalyzed transformations. His group has been centered in the development of sustainable synthetic methods, by using microwave irradiation and solvent free conditions; more recently the group developed the first static ohmic heating reactor for chemical synthesis at laboratory scale, a high energy-efficient way of heating chemical reactions using water as solvent. Using this alternative heating method, new protocols for the synthesis of relevant compounds have already been successfully developed. His research interests also include the isolation and structural characterization of natural products from diverse terrestrial and marine sources.

He graduated from Kyoto University in 1970

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