Journal of Organic Chemistry p. 1146 - 1157 (2020)
Update date:2022-08-15
Topics:
Boichenko, Maksim A.
Andreev, Ivan A.
Chagarovskiy, Alexey O.
Levina, Irina I.
Zhokhov, Sergey S.
Trushkov, Igor V.
Ivanova, Olga A.
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.
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