63075-55-8Relevant academic research and scientific papers
Conjugate addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system
Kitamura, Masato,Miki, Takashi,Nakano, Keiji,Noyori, Ryoji
, p. 5141 - 5144 (1996)
In the presence of a Cu(I)-N-monosubstituted sulfonamide combined catalyst system, diorganozincs react with α,β-unsaturated ketones to generate Zn enolates, which may be hydrolyzed, giving the β-substituted ketones, or used for further aldol reaction or Pd(O)-catalyzed reaction with allyl acetate leading to the regiospecific α,β-vicinal condensation products.
Copper-catalysed conjugate addition of grignard reagents to 2-methylcyclopentenone and sequential enolate alkylation
Calvo, Beatriz C.,Madduri, Ashoka V. R.,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.
, p. 2061 - 2069 (2014/07/07)
The copper/Rev-JosiPhos-catalysed asymmetric conjugate addition of Grignard reagents to 2-methylcyclopentenone (1) provides 2,3-disubstituted cyclopentanones in high yields and enantioselectivities, and good diastereoselectivities. Reaction of the in situ
STEREOCHEMISTRY OF THE C3 ADDITION OF 1-LITHIO 1,1-BIS METHYLSELENOALKANES TO METHYL CYCLOHEXENONES
Lucchetti, J.,Krief, A.
, p. 1623 - 1626 (2007/10/02)
The presence of DME or HMPT allows the C3 regio and stereoselective introduction of 1,1-bis methylselenoalkanes to methyl cyclohexenones.The resulting compounds have been stereoselectively transformed to 3-ethyl methyl cyclohexanones.
"1,4" Alkyl Migrations in Fischer Indole Cyclizations
Miller, Bernard,Matjeka, Edward R.
, p. 4772 - 4780 (2007/10/02)
The product from Fisher indole cyclization and dehydrogenation of cyclohexanone 2,4,6-trimethylphenylhydrazone (1) was determined to be 2,3,4-trimethylcarbazole (3) resulting from a formal 1,4-methyl migration, as previously proposed.To determine the destinations of migrating groups in these rearrangements, the Fischer indole cyclization and dehydrogenation of cyclohexanone 2-ethyl-6-methylphenylhydrazone (17) were studied.The products obtained were 1-ethylcarbazole, 1-methylcarbazole, 2-ethyl-1-methylcarbazole (18), and an apparent mixture of 1-ethyl-4-methylcarbazole (21) and 4-ethyl-1-methylcarbazole (22).However, no 1-ethyl-2-methylcarbazole (19), which would have been obtained by a "1,4"-methyl migration, was obtained.Analysis of the product ratios suggested that the apparent ethyl shift in formation of 18 actually proceeded by a formal shift of either an ethyl or a methyl group, followed by a ethyl shift.Cyclization of 3-pentanone 2,4,6-trimethylphenylhydrazone (26) proceeded to give the product of "1,4" methyl migration, demonstrating that such reactions can occur with phenylhydrazones of ketones other than cyclohexanone.It is proposed that steric factors play a major role in determining whether migrating groups undergo or "1,4" shifts during Fischer indole cyclizations.
