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

28 August 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

azetidine
penaresidin B
C-H Amination
Intermolecular C-H amination
azetidine synthesis
nitrogen heterocycle synthesis

Supplementary materials

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Supporting Information - azetidine final draft 082619
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