76757-06-7

Upstream product

• 1189-04-4 N-methyl-3-methyl-2-butenamide 
• 100-39-0 benzyl bromide 
• 74-89-5 methylamine 
• 2550-26-7 4-Phenyl-2-butanone 
• 72681-05-1 (E/Z)-3-methyl-5-phenylpent-2-enoic acid 

Downstream Products

• 136962-54-4 (R)-N,3-dimethyl-5-phenylpentanamide 
• 136962-57-7 (S)-N,3-dimethyl-5-phenylpentanamide 

Relevant academic research and scientific papers

Enantioselective Conjugate Reduction of α,β-Unsaturated Carboxamides with Semicorrin Cobalt Catalysts

Chiral semicorrin cobalt complexes, prepared in situ from cobalt(II) chloride and the free ligands, are efficient, highly enantioselective catalysts for the conjugate reduction of α,β-unsaturated carboxamides with sodium borohydride.Enantiomeric excesses of up to 99percent, essentially quantitative yields, and high substrate/catalyst ratios (1000-10 000:1) are attractive attributes of this catalytic process.

Metalated Unsaturated Amides. Regio- and Stereoselective γ-Alkylation

The reactions of lithiated and dilithiated unsaturated amides 4, 5, 12, 15, 18, 34, and 36 with a variety of electrophiles have been shown to produce deconjugated, α-alkylated products 6, 7, 13, 16, 19, 35, and 37, respectively, in good to excellent yields (Tables I, II, IV, and VI).Whereas lithiated 4 and dilithiated 5 do not undergo γ-alkylation, the corresponding species of 12 and 15, when converted to their cuprates by using cuprous iodide, afford γ products 4 and 17 with good regio- (67-90percent) and Z stereoselectivity (67-80percent) for E = allyl, prenyl, and geranyl.Differences between the reactions of cuprated, unsaturated amides and unsaturated carboxylic acids with nonallylic alkylating agents are discussed.The reaction of dicuprated N-methylsenecioamide (15) with prenyl bromide leads to a complex mixture of products which have been separated and characterized (Scheme III).The reaction of lithiated N,N-dimethylsenecioamide (18) with aromatic and pyridine aldehydes and some ketones has been shown to provide α (19) or γ (20) products, depending on the conditions of the reaction (Table VI).In this reaction, the reversible formation of the α product 19 and its conversion into the γ product 20 have been demonstrated (Scheme IV).The utility of the α- and γ-alkylated unsaturated amide products is illustrated by the syntheses of the monoterpenoid lavandulol (42) and the amide alkaloid piperlonguminine (43), respectively.