Asymmetric Aminalization via Cation-Binding Catalysis

Sang Yeon Park; Yidong Liu; Joong Suk Oh; Yoo Kyung Kweon; Yong Bok Jeong; Yu Tan; Ji-Woong Lee; Hailong Yan; Choong Eui Song

doi:10.1002/chem.201703800

Asymmetric Aminalization via Cation-Binding Catalysis

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

Kemisk Institut

12 Citationer (Scopus)

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.

Originalsprog	Engelsk
Tidsskrift	Chemistry: A European Journal
Vol/bind	24
Udgave nummer	5
Sider (fra-til)	1020-1025
Antal sider	6
ISSN	0947-6539
DOI	https://doi.org/10.1002/chem.201703800
Status	Udgivet - 24 jan. 2018

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10.1002/chem.201703800

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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.",

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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}",

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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

PY - 2018/1/24

Y1 - 2018/1/24

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

SN - 0947-6539

VL - 24

SP - 1020

EP - 1025

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 5

ER -

Asymmetric Aminalization via Cation-Binding Catalysis

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