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Highly Enantioselective Synthesis of Acyclic N, N'-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines.

08:00 EDT 2nd July 2019 | BioPortfolio

Summary of "Highly Enantioselective Synthesis of Acyclic N, N'-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines."

N, N'-Acetals are sensitive compounds, and the challenging asymmetric synthesis of acyclic N, N'-acetals by the general addition of amines to ketimines has never been reported so far. In this study, highly enantioselective addition of aryl amines to isatin-derived ketimines catalyzed by chiral urea derived from quinine was developed. A series of new acyclic N, N'-acetals were constructed by this protocol in high to excellent yields (78-99%) and high to excellent enantioselectivities (76-96% ee).

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Name: Organic letters
ISSN: 1523-7052
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Medical and Biotech [MESH] Definitions

Diethers with the structure -C(OR'')(OR'''), where R'' and R''' are not hydrogen. Mixed acetals have R'' and R''' groups which differ.

Polymers of N-SUBSTITUTED GLYCINES containing chiral centers at the a-position of their side chains. These oligomers lack HYDROGEN BONDING donors, preventing formation of the usual intrachain hydrogen bonds but can form helices driven by the steric influence of chiral side chains.

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An amino acid produced in the urea cycle by the splitting off of urea from arginine.

Enzymes that catalyze the epimerization of chiral centers within carbohydrates or their derivatives. EC 5.1.3.

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