Acid-mediated ring-expansion of 2,2-disubstituted azetidine carbamates to 6,6-disubstituted 1,3-oxazinan-2-ones
File(s)MS Azetidine Expansion Submission Revised.pdf (657.74 KB)
Accepted version
Author(s)
Type
Journal Article
Abstract
The ring expansion of 2-ester-2-aryl-azetidine carbamates can be achieved using Brønsted acids to form 6,6-disubstituted 1,3-oxazinan-2-ones. The reaction is rapid at room temperature with Boc or Cbz derivatives, and proceeds with excellent yield (up to 96%) and broad substrate scope. Derivatives of drug compounds and natural products are incorporated. The combina-tion of this ring expansion in a 3-step N–H insertion/cyclization/expansion (NICE) sequence is applied to directly access medicinally relevant scaffolds from acyclic precursors.
Date Issued
2019-03-15
Date Acceptance
2019-02-27
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
1818
End Page
1822
Journal / Book Title
Organic Letters
Volume
21
Issue
6
Copyright Statement
© 2019 American Chemical Society
Sponsor
The Royal Society
The Royal Society
The Royal Society
Grant Number
UF140161
RG150444
RGF\EA\180031
Subjects
03 Chemical Sciences
Organic Chemistry
Publication Status
Published
Date Publish Online
2019-03-04