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Intermolecular sp3-C–H Amination for the Synthesis of Saturated Azacycles

preprint
submitted on 27.08.2019, 01:06 and posted on 28.08.2019, 17:18 by Kerry Betz, Nicholas Chiappini, Justin Du Bois
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 is 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 2° amines. The preparative convenience of this protocol is demonstrated through gram-scale and telescoped multi-step procedures. Application of this technology is highlighted in a nine step total synthesis of an unusual azetidine-containing natural product, penaresidin B.

Funding

NSF-CCHF (CHE-1700982)

Evelyn Laing McBain Fellowship

National Science Foundation for a Graduate Research Fellowship

History

Email Address of Submitting Author

ndchiappi@stanford.edu

Institution

Stanford University

Country

United States of America

ORCID For Submitting Author

0000-0003-0469-1008

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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