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7738970 
Journal Article 
Monoprotected Diamines Derived from 1,5-Disubstituted (Aza)spiro[2.3]hexane Scaffolds 
Malashchuk, A; Chernykh, AV; Perebyinis, MY; Komarov, IV; Grygorenko, OO 
2021 
Yes 
European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690 
Wiley-VCH Verlag 
English 
WOS:000621843600001 
Synthesis of monoprotected diamines derived from 1,5-disubstituted spiro[2.3]hexane and 5-azaspiro[2.3]hexane scaffolds is described. In both cases, the method relied on the cyclopropanation of the corresponding cyclobutane or azetidine derivatives. In the case of monoprotected 1,5-diaminospiro[2.3]hexanes, the title products were obtained as single diastereomers. X-Ray diffraction studies supported by exit vector plot (EVP) analysis showed that the obtained building blocks are promising piperidine/cycloalkane isosteres with potential utility to drug discovery. Also, conformations observed in the crystalline state for the two different diastereomers of 1,5-diaminospiro[2.3]hexane derivatives prompt their application in design of β-turn and sheet-like peptidomimetics, respectively. © 2021 Wiley-VCH GmbH 
Diamines; Exit vector plots; Molecular rigidity; Peptidomimetics; Spirocyclic compounds