Synthesis of 1- and 1,2-Substituted Cyclopropylamines from Ketone Homoenolates.

Autor:	West MS; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada., Pia JE; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada., Rousseaux SAL; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2022 Aug 19; Vol. 24 (32), pp. 5869-5873. Date of Electronic Publication: 2022 Jul 06.
DOI:	10.1021/acs.orglett.2c01634
Abstrakt:	Ketone homoenolates are intermediates with both nucleophilic and electrophilic properties. While there are several reports on their use as nucleophiles, there are few reports on their potential as electrophiles. Herein, we report the use of ketone zinc/copper homoenolates as electrophiles in the synthesis of 1- and 1,2-substituted cyclopropylamines. We found that CuCN·2LiCl is essential to produce a more reactive homoenolate intermediate. We also report a facile telescoped sequence from β-substituted enones toward 1,2-disubstituted cyclopropylamines.
Databáze:	MEDLINE
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