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Asymmetric synthesis of 1-substituted 2-azaspiro[3.3]heptanes: important motifs for modern drug discovery†
Leleti Rajender Reddy,Yogesh Waman,Priya Kallure,Kumara Swamy Nalivela,Zubeda Begum,Thumbar Divya,Sharadsrikar Kotturi
Chemical Communications Pub Date : 03/07/2019 00:00:00 , DOI:10.1039/C9CC00863B
Abstract

Highly diastereoselective addition of ethyl cyclobutanecarboxylate anions to Davis–Ellman's imines is reported. This methodology afforded the preparation of enantiomerically and diastereomerically pure 1-substituted 2-azaspiro[3.3]heptanes. This three-step procedure proceeded efficiently (yield up to 90%) and diastereoselectively (dr values up to 98 : 2). This methodology is applicable to the synthesis of 1-substituted 2-azaspiro[3.4]octane and 1-substituted 2-azaspiro[3.5]nonane.

Graphical abstract: Asymmetric synthesis of 1-substituted 2-azaspiro[3.3]heptanes: important motifs for modern drug discovery
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