Memory of chirality trapping of low inversion barrier 1,4-benzodiazepin-2-one enolates |
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| Institution: | 1. Department of Chemistry, Baselius College, Kottayam 686001, Kerala, India;2. School of Health Science, University of KwaZulu-Natal, Westville, Durban 4001, South Africa;3. Division of Drug Design and Medicinal Chemistry Research Lab, Department of Pharmaceutical Chemistry, Ahalia School of Pharmacy, Palakkad 678557, Kerala, India;4. School of Pure & Applied Physics, MG University, 686560, Kerala, India;5. Department of Chemistry, Sree Narayana College, Thrissur 680566, Kerala, India;1. Department of Chemistry, Dibrugarh University, Dibrugarh 786004, Assam, India;2. Department of Chemistry, Rajiv Gandhi University, Doimukh, Rono Hills, Itanagar 791112, Arunachal Pradesh, India;1. China University of Mining and Technology, Xuzhou, China;2. GCL-POLY Energy Holdings Limited (PV), Suzhou, China;3. GCL Technology Research Center, Richland, USA;4. Suzhou GCL Photovoltaic Technology Co., Ltd., Suzhou, China |
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| Abstract: | We have previously demonstrated that chiral, enantiopure 3-substituted 1,4-benzodiazepin-2-ones undergo retentive deprotonation/trapping at −78 °C, if the N1-substituent is sufficiently large (e.g., i-Pr). Stereocontrol in this reaction is attributed to the formation of an enantiopure, conformationally chiral enolate; at −78 °C a large N1 substituent (e.g., i-Pr) is needed to impart a sufficient barrier to enolate racemization. Herein, we report strategies to achieve high enantiomeric excess in deprotonation/alkylation of low inversion barrier 1,4-benzodiazepin-2-ones featuring small N1 substituents. |
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