Straightforward Synthetic Approach to Aminoalcohols with 9-oxabicyclo[3.3.1]nonane or Cyclooctane Core via Nucleophilic Ring-Opening of Spirocyclic Bis(oxiranes)
Olga V. Ryzhikova, Daiana V. Savchenkova, Sergey V. Kositov, Yuri K. Grishin, Olga A. Maloshitskaya, Kseniya N. Sedenkova, Elena B. Averina
TL;DR
This paper presents a new method to synthesize aminoalcohols using ring-opening reactions of spirocyclic bis(oxiranes) with amines.
Contribution
A straightforward, stereoselective synthesis of aminoalcohols with specific cyclic cores via nucleophilic ring-opening.
Findings
Trans-isomer produces aminoalcohols with a 9-oxabicyclo[3.3.1]nonane core through a domino process.
Cis-isomer yields aminosubstituted cis-cyclooctane-1,5-diols from independent oxirane reactions.
LiClO4 activation enables use of various amines in the ring-opening process.
Abstract
Nucleophilic ring-opening of bis(oxiranes), containing several reactive centers, can be used to elaborate straightforward atom-economy and stereoselective approaches to polyfunctionalized compounds. In the present work, ring-opening of cis- and trans-diastereomers of a spirocyclic bis(oxirane), containing a cyclooctane core (namely, 1,8-dioxadispiro[2.3.2.3]dodecane), upon treatment with various amines, was studied. Trans-isomer afforded aminoalcohols with 9-oxabicyclo[3.3.1]nonane moiety, formed via domino-process, including opening of an oxirane ring followed by intramolecular cyclization. Ring-opening of cis-isomer gave aminosubstituted cis-cyclooctane-1,5-diols, derived from independent reaction of two oxirane moieties. Activation of oxirane rings by the addition of LiClO4, acting as a Lewis acid, allowed the involvement of a number of primary and secondary aliphatic amines as well…
Genes, proteins, chemicals, diseases, species, mutations and cell lines named across the full text — each resolved to its canonical identifier and authoritative record.
Click any figure to enlarge with its caption.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14
Figure 15
Figure 16
Figure 17
Figure 18
Figure 19
Figure 20
Figure 21Peer Reviews
No public reviews on file for this paper yet. If you reviewed it on a platform where reviews are public (OpenReview, ICLR, NeurIPS, ICML), you can paste yours below so the community can read it here.
Videos
No videos yet. Explain this paper in a talk, walkthrough, or lecture? Add one.
Taxonomy
TopicsSynthesis and Catalytic Reactions · Cyclopropane Reaction Mechanisms · Click Chemistry and Applications