Enantioselective Grignard addition to nitroolefin

Vinyl Esters as Acetaldehyde Surrogates: Potential Utility in Some Common Multicomponent Sequences

“…Reaction of phthalhydrazide (14), vinyl acetate (2 a) and malonitrile (15) also didn't work at all and starting material was recovered ( Figure 8). [46] The similar acylated products of 2-naphthol (18) and aniline (22) were obtained in all other MCR sequences surveyed (Figure 9). [47][48][49][50][51][52][53] Finally, we compared vinyl acetate with enol ethers for their utility as aldehyde equivalents.…”

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

“…[114][115][116][117][118][119][120][121][122][123][124][125] O-Alkylation of nitroalkanesunder basic conditions affords the corresponding alkyln itronates which can be hydrolyzed to the parent carbonyl compounds under basic conditions. [126] Am odern variant of this Scheme 52.…”

Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence

“…To avoid this bottleneck, we penciled down an alternative design, in which nitronic acid 8 would be generated in a one-pot fashion aer conjugate nucleophilic addition of Grignard reagents to nitro-olen 6. [18][19][20][21][22][23][24][25][26] When only the diversication of the R 3 substituent is pursued, structure 6 could serve as a common intermediate, prepared in a single scaled-up experiment via Henry reaction of readily available 3-indolylaldehyde 10 (Scheme 2). To test this idea, (E)-3-(2-nitrovinyl)-2-phenyl-1H-indole (6a) was subjected to a reaction with phenylmagnesium bromide (7a) in dry THF.…”