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3‐Bromo N ‐Alkyl Cyanamides as Versatile Building Blocks
Author(s) -
Wright Karen,
Drouillat Bruno,
Menguy Laurence,
Marrot Jérôme,
Couty François
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801439
Subject(s) - alkyl , cyanamide , cyanogen bromide , electrophile , combinatorial chemistry , bromide , chemistry , organic chemistry , catalysis , biochemistry , peptide sequence , gene
3‐Bromo N ‐alkyl cyanamides are accessible in one simple synthetic operation from N ‐alkyl azetidines reacting with cyanogen bromide. These unexplored building blocks combine two extremely useful electrophilic moieties: an alkyl bromide and a cyanamide. We demonstrate herein that they can be transformed into a range of nitrogen‐containing molecules, and especially cyclic guanidines, accessible in enantiomerically pure form. Considering the large structural diversity of available azetidines, this contribution complements the use of these strained heterocycles in diversity‐oriented synthesis.