Asymmetric Aminalization via Cation-Binding Catalysis
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Asymmetric Aminalization via Cation-Binding Catalysis. / Park, Sang Yeon; Liu, Yidong; Oh, Joong Suk; Kweon, Yoo Kyung; Jeong, Yong Bok; Tan, Yu; Lee, Ji-Woong; Yan, Hailong; Song, Choong Eui.
I: Chemistry: A European Journal, Bind 24, Nr. 5, 2018, s. 1020-1025.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Asymmetric Aminalization via Cation-Binding Catalysis
AU - Park, Sang Yeon
AU - Liu, Yidong
AU - Oh, Joong Suk
AU - Kweon, Yoo Kyung
AU - Jeong, Yong Bok
AU - Tan, Yu
AU - Lee, Ji-Woong
AU - Yan, Hailong
AU - Song, Choong Eui
N1 - © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2018
Y1 - 2018
N2 - Asymmetric cation-binding catalysis, in principle, can generate "chiral" anionic nucleophiles, where the counter cations are coordinated within chiral environments. Nitrogen-nucleophiles are intrinsically basic, therefore, its use as nucleophiles is often challenging and limiting the scope of the reaction. Particularly, a formation of configurationally labile aminal centers with alkyl substituents has been a formidable challenge due to the enamine/imine equilibrium of electrophilic substrates. Herein, we report enantioselective nucleophilic addition reactions of potassium phthalimides to Boc-protected alkyl- and aryl-substituted α-amido sulfones. In-situ generated imines smoothly reacted with the nitrogen nucleophiles to corresponding aminals with good to excellent enantioselectivitiy under mild reaction conditions. In addition, transformation of aminal products gave biologically relevant pyrrolidinone-fused hexahydropyrimidine scaffold with excellent stereoselectivity and good yield.
AB - Asymmetric cation-binding catalysis, in principle, can generate "chiral" anionic nucleophiles, where the counter cations are coordinated within chiral environments. Nitrogen-nucleophiles are intrinsically basic, therefore, its use as nucleophiles is often challenging and limiting the scope of the reaction. Particularly, a formation of configurationally labile aminal centers with alkyl substituents has been a formidable challenge due to the enamine/imine equilibrium of electrophilic substrates. Herein, we report enantioselective nucleophilic addition reactions of potassium phthalimides to Boc-protected alkyl- and aryl-substituted α-amido sulfones. In-situ generated imines smoothly reacted with the nitrogen nucleophiles to corresponding aminals with good to excellent enantioselectivitiy under mild reaction conditions. In addition, transformation of aminal products gave biologically relevant pyrrolidinone-fused hexahydropyrimidine scaffold with excellent stereoselectivity and good yield.
KW - Journal Article
U2 - 10.1002/chem.201703800
DO - 10.1002/chem.201703800
M3 - Journal article
C2 - 28833708
VL - 24
SP - 1020
EP - 1025
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 5
ER -
ID: 182536793