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J Org Chem. 2020 Jan 17;85(2):1146-1157. doi: 10.1021/acs.joc.9b03098. Epub 2019 Dec 19.

Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates.

Author information

1
Department of Chemistry , M. V. Lomonosov Moscow State University , Leninskie gory 1-3 , Moscow 119991 , Russian Federation.
2
N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences , Leninsky pr. 47 , Moscow 119991 , Russian Federation.
3
Laboratory of Chemical Synthesis, Dmitry Rogachev National Medical Research Center of Pediatric Hematology , Oncology and Immunology , Samory Mashela 1 , Moscow 117997 , Russian Federation.
4
N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences , Kosygina 4 , Moscow 119334 , Russian Federation.

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(C6F5)3 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 SN2 conditions led to the formation of 2-arylsuccinonitriles.

PMID:
31804074
DOI:
10.1021/acs.joc.9b03098

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