81852-03-1Relevant academic research and scientific papers
Intermolecular sp3-C-H Amination for the Synthesis of Saturated Azacycles
Betz, Kerry N.,Chiappini, Nicholas D.,Du Bois
supporting information, p. 1687 - 1691 (2020/01/09)
The preparation of substituted azetidines and larger ring, nitrogen-containing saturated heterocycles is enabled through efficient and selective intermolecular sp3-C-H amination of alkyl bromide derivatives. A range of substrates are demonstrated to undergo C-H amination and subsequent sulfamate alkylation in good to excellent yield. N-Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions to yield the corresponding cyclic secondary amines. The preparative convenience of this protocol is demonstrated through gram-scale and telescoped multistep procedures. Application of this technology is highlighted in a nine-step total synthesis of an unusual azetidine-containing natural product, penaresidin B.
