Captodative aminoalkenes

The Wonderful Chemistry of Trifluoromethyl α‐Haloalkenyl Ketones

“…Evidently, the assembly of indenol derivatives is initiated by protonation of the carbonyl group in the enone 1 or 7 , followed by intramolecular electrophilic aromatic substitution resulting in the formation of the appropriate carbocycle 8 . In contrast, captodative aminoenones are generally reactive enough without any additional acid catalyst , …”

Domino Transformations of gem‐Trifluoroacetyl(bromo)alkenes under the Action of Secondary Amines

“…[1] Their attraction is caused by remarkable and specific reactivity that is different from simple enamines and α,β-unsaturated aldehydes, ketones, and esters. These unique kinds of enamines have been used as versatile building blocks in the synthesis of various biologically important heterocycles and analogs of natural substances.…”

“…This strategy is universal and very attractive because of its experimental simplicity and availability of the starting compounds. Previously, this methodology was successfully applied to the synthesis of various captodative aminoalkenes containing a carbonyl-, formyl-, or alkoxycarbonyl functional group [1,6] as an electron-withdrawing group and including derivatives having a slow basic tertiary amino group as well as a terminal double bond. [7] It is interesting to remark that only the β-alkoxy group has been regiospecifically substituted with secondary or primary amines in their reactions with β-butoxy-α-bromovinyl trifluoromethyl ketone.…”

Assembly of Trifluoromethylated Morpholines through Cascade Reactions of Bromoenones with Secondary Amino Alcohols

“…The addition of diethylamine (2 equiv.) to a CD 3 CN solution of hemiacetal led to the rapid appearance of signals characteristic of indene; it has previously been shown that the formation of this compound occurs through a sequence of addition, nucleophilic substitution, elimination, and electrophilic substitution , …”