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Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2020 Jan 17; Vol. 85 (2), pp. 1146-1157. Date of Electronic Publication: 2019 Dec 19. - Publication Year :
- 2020
-
Abstract
- A straightforward method for ring opening of donor-acceptor cyclopropanes with trimethylsilyl cyanide as a surrogate of cyanide ion in the presence of B(C <subscript>6</subscript> F <subscript>5</subscript> ) <subscript>3</subscript> or trifluoromethanesulfonic acid as a catalyst has been developed. The methodology provides a short route to γ-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive molecules such as glutaric and δ-aminovaleric acid derivatives, 3-arylpiperidines, or other substituted phenethylamines. Oppositely, the attempts to synthesize these γ-cyanoesters by direct reaction of cyclopropanes with sodium cyanide under typical S <subscript>N</subscript> 2 conditions led to the formation of 2-arylsuccinonitriles.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 85
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31804074
- Full Text :
- https://doi.org/10.1021/acs.joc.9b03098