Year: 2025
Type: dissertation
Abstract: Many biologically active compounds, including pharmaceuticals, are optically active and often only one of the enantiomer shows a high biologically activity. Therefore, it is important to develop the synthetic methodology for providing only necessary enantiomer. As the methodology, catalytic asymmetric synthesis, in which the use of a low amount of a chiral catalyst theoretically enables infinite production of optically active compounds, is the most efficient in the synthetic organic chemistry field. Moreover, this methodology is also important in terms of energy saving and environmental friendliness. The chiral catalysts used in catalytic asymmetric syntheses can be divided into two categories of organometallic catalyst and metal-free organocatalyst. Particularly, organocatalyst is stable in air, easy to handle, and inexpensive, so they are being focused on as next-generation, environmentally friendly catalysts. Author developed the new cage-typed 2-azanorbornane-based amino amide organocatalyst. This catalyst is expected to work as multipoint recognition catalyst having both covalent and non-covalent hydrogen bonding sites in the single molecule. This catalyst was successfully derived from commercially available amino acids, and the excellent catalytic activities were demonstrated in the Michael addition. The enantioselective asymmetric Michael reaction of β-keto esters with nitro olefins using 2-azanornane-based amino amide organocatalysts was carried out to provide chiral Michael adducts in excellent chemical yields, diastereoselectivities and enantioselectivities. The obtained Michael adducts with chiral quaternary carbon center are important synthetic precursors of the synthesis of many biologically active compounds including pharmaceuticals such as platencin (antibiotic). In this study, author revealed that the new explored cage-typed amino amide organocatalyst showed satisfactory catalytic activities in the Michael addition. It is expected that this result should be able to greatly contribute the development of new drug and its related compounds.
DOI: 10.15118/0002000406
Authors: HUANG, YUEMING, ホアン, ユエミン
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7111134016
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