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

Harvard

Park, SY, Liu, Y, Oh, JS, Kweon, YK, Jeong, YB, Tan, Y, Lee, J-W, Yan, H & Song, CE 2018, 'Asymmetric Aminalization via Cation-Binding Catalysis', Chemistry: A European Journal, bind 24, nr. 5, s. 1020-1025. https://doi.org/10.1002/chem.201703800

APA

Park, S. Y., Liu, Y., Oh, J. S., Kweon, Y. K., Jeong, Y. B., Tan, Y., Lee, J-W., Yan, H., & Song, C. E. (2018). Asymmetric Aminalization via Cation-Binding Catalysis. Chemistry: A European Journal, 24(5), 1020-1025. https://doi.org/10.1002/chem.201703800

Vancouver

Park SY, Liu Y, Oh JS, Kweon YK, Jeong YB, Tan Y o.a. Asymmetric Aminalization via Cation-Binding Catalysis. Chemistry: A European Journal. 2018;24(5):1020-1025. https://doi.org/10.1002/chem.201703800

Author

Park, Sang Yeon ; Liu, Yidong ; Oh, Joong Suk ; Kweon, Yoo Kyung ; Jeong, Yong Bok ; Tan, Yu ; Lee, Ji-Woong ; Yan, Hailong ; Song, Choong Eui. / Asymmetric Aminalization via Cation-Binding Catalysis. I: Chemistry: A European Journal. 2018 ; Bind 24, Nr. 5. s. 1020-1025.

Bibtex

@article{d125c3f55e574e828208cfea9f84fb5f,

title = "Asymmetric Aminalization via Cation-Binding Catalysis",

abstract = "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.",

keywords = "Journal Article",

author = "Park, {Sang Yeon} and Yidong Liu and Oh, {Joong Suk} and Kweon, {Yoo Kyung} and Jeong, {Yong Bok} and Yu Tan and Ji-Woong Lee and Hailong Yan and Song, {Choong Eui}",

note = "{\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2018",

doi = "10.1002/chem.201703800",

language = "English",

volume = "24",

pages = "1020--1025",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "5",

}

RIS

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

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