124306-47-4Relevant academic research and scientific papers
Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: Enantioselective synthesis of substituted 3-hydroxy-2-oxindoles
Laina-Martín, Víctor,Humbrías-Martín, Jorge,Fernández-Salas, José A.,Alemán, José
supporting information, p. 2781 - 2784 (2018/03/21)
A highly enantioselective organocatalytic vinylogous Mukaiyama aldol reaction of silyloxy dienes and isatins under bifunctional organocatalysis is presented. Substituted 3-hydroxy-2-oxindoles are synthesised in good yields and enantioselectivities. These
Reaction of acylsilanes with α-sulfinyl carbanions: Regioselective synthesis of silyl enol ethers
Honda, Mitsunori,Nakajima, Tadashi,Okada, Maiko,Yamaguchi, Keita,Suda, Mitsuhiro,Kunimoto, Ko-Ki,Segi, Masahito
experimental part, p. 3740 - 3742 (2011/08/06)
The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding unsymmetrical ketones with base.
Lewis base activation of Lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions
Denmark, Scott E.,Heemstra Jr., John R.
, p. 5668 - 5688 (2008/02/10)
(Chemical Equation Presented) The generality of Lewis base catalyzed, Lewis acid mediated, enantioselective vinylogous aldol addition reactions has been investigated. The combination of silicon tetrachloride and chiral phosphoramides is a competent catalyst for highly selective additions of a variety of α,β-unsaturated ketone-, 1,3-diketone-, and α,β- unsaturated amide-derived dienolates to aldehydes. These reactions provided high levels of γ-site selectivity for a variety of substitution patterns on the dienyl unit. Both ketone- and morpholine amide-derived dienol ethers afforded high enantio- and diastereoselectivity in the addition to conjugated aldehydes. Although α,β-unsaturated ketone-derived dienolate did not react with aliphatic aldehydes, α,β-unsaturated amide-derived dienolates underwent addition at reasonable rates affording high yields of vinylogous aldol product. The enantioselectivities achieved with the morpholine derived-dienolate in the addition to aliphatic aldehydes was the highest afforded to date with the silicon tetrachloride-chiral phosphoramide system. Furthermore, the ability to cleanly convert the morpholine amide to a methyl ketone was demonstrated.
