Journal
ORGANIC LETTERS
Volume 22, Issue 5, Pages 1687-1691Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04096
Keywords
-
Categories
Funding
- National Science Foundation under the Center for Chemical Innovation in Selective C-H Functionalization [CHE-1700982]
- Novartis Pharmaceuticals
- Evelyn Laing McBain Fellowship
- National Science Foundation
Ask authors/readers for more resources
The preparation of substituted azetidines and larger ring, nitrogen-containing saturated heterocycles is enabled through efficient and selective intermolecular sp(3)-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available