Seoul National University · Chemistry
Professor Hyeung-geun Park's research lab specializes in the development of innovative organocatalytic methodologies, with a primary focus on chiral phase-transfer catalysis for asymmetric synthesis. The lab pioneers the design and application of Cinchona alkaloid-derived catalysts to enable enantioselective transformations under mild, practical conditions—critical for industrial scalability. Key research directions include the synthesis of chiral α-amino acids, spirooxindole natural products, and versatile chiral building blocks through catalytic alkylation, allylation, and aza-Michael reactions. The lab emphasizes atom-economical, high-yielding, and enantioselective routes suitable for large-scale applications in pharmaceutical and fine chemical synthesis.
Figures are computed from collected data and may differ slightly.
Phase-transfer catalysis is one of the most useful methodologies for practical syntheses given its operational simplicity and mild reaction conditions that enable its application in industrial processes. Cinchona alkaloids have been a popular, natural source of practical organocatalysts due largely to their excellent commercial availability and low cost. Since the first Cinchona alkaloid-derived phase-transfer catalysts was disclosed in 1981, diverse generations of Cinchona-derived phase-transfe
A dimeric Cinchona alkaloid ammonium salt, α,α′-bis[O(9)-allylcinchonidinium]-m-x ylene dibromide 4, has been developed as a new efficient phase-transfer catalyst; the catalytic enantioselective alkylation of N-(diphenylmethylene)glycine tert-butyl ester using 4 provided 7 in a high enantiomeric excess (90–99% ee).
Potenzielle Katalysatoren für industrielle Syntheseprozesse zur Herstellung natürlicher und nichtnatürlicher chiraler α-Aminosäuren sind die dimeren, auf Naphthalin basierenden Cinchona-Alkaloide 1 aufgrund der milden Reaktionsbedingungen und hohen katalytischen Effizienz (hohe Ausbeuten und ee-Werte). Sie fungieren als Phasentransferkatalysatoren bei der Alkylierung eines Glycin-Derivats. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2
A new efficient and concise enantioselective synthetic method for (-)-horsfiline is reported. (-)-Horsfiline could be obtained from diphenylmethyl tert-butyl malonate in 9 steps (32%,>99% ee) by using the enantioselective phase-transfer catalytic allylation (91% ee) as the key step. This approach can be applied as a practical route for the large-scale synthesis of spirooxindole natural products, which enables a systematic investigation of their biological activity to be performed.
The phase-transfer catalytic alkylation of N,N-dialkylmalonamic tert-butyl esters in the presence of 1 mol% of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded highly enantioselective (S)-mono-alpha-alkylated products (up to 96% ee), which could be readily converted into versatile chiral building blocks without loss of chirality.
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