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

Ring Opening of Donor–Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2020, Volume: 85, Number: 2, Pages: 1146-1157 Pages count : 12 DOI: 10.1021/acs.joc.9b03098

Authors

Boichenko Maksim A ¹ , Andreev Ivan A ^2,3 , Chagarovskiy Alexey O ^2,3 , Levina Irina I ⁴ , Zhokhov Sergey S ¹ , Trushkov Igor V ^2,3 , Ivanova Olga A ^1,2

Affiliations

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

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.

Boichenko M.A. , Andreev I.A. , Chagarovskiy A.O. , Levina I.I. , Zhokhov S.S. , Trushkov I.V. , Ivanova O.A.
Ring Opening of Donor–Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
Journal of Organic Chemistry. 2020. V.85. N2. P.1146-1157. DOI: 10.1021/acs.joc.9b03098 WOS Scopus OpenAlex

Web of science:	WOS:000508468900077
Scopus:	2-s2.0-85076992071
OpenAlex:	W2992402637

DB	Citing
OpenAlex	32
Scopus	31
Web of science	29