Michael Cascade Research Articles

ChemInform Abstract: Asymmetric Synthesis of Spiro[chroman‐3,3′‐pyrazol] Scaffolds with an All‐Carbon Quaternary Stereocenter via a Oxa‐Michael—Michael Cascade Strategy with Bifunctional Amine‐Thiourea Organocatalysts.

AbstractIt is shown that the thiourea moiety and cyclohexyl scaffold of the employed bifunctional catalyst play a significant role in controlling the stereoselectivity of the oxa‐Michael‐Michael cascade reaction.

ChemInform Abstract: Enantioselective Synthesis of Highly Substituted Chromans via the Oxa‐Michael—Michael Cascade Reaction with a Bifunctional Organocatalyst.

A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael–Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).

Current advances of organocatalytic Michael–Michael cascade reaction in the synthesis of highly functionalized cyclic molecules

Organocatalytic domino/cascade reactions provide a convenient method for the construction of highly functionalized cyclic molecular structures bearing multiple stereocenters in a highly stereoselective fashion.

Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst.

A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).

ChemInform Abstract: Asymmetric One‐Pot Synthesis of 1,4‐Dihydroquinolines via an Organocatalytic Aza‐Michael/Michael Cascade Strategy.

AbstractThe asymmetric aza‐Michael/Michael cascade reaction of 2‐(tosylamino)phenyl substituted α,β‐unsaturated ketones with arylpropionaldehydes is optimized using a catalyst combination of O‐Tms‐diphenylprolinol and o‐nitrobenzoic acid.

ChemInform Abstract: One‐Pot Catalytic Enantioselective Synthesis of Functionalized Tetrahydroquinolines by Aza‐Michael/Michael Cascade Reactions of N‐Protected 2‐Aminophenyl α,β‐Unsaturated Esters with Nitroolefins.

A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).

Asymmetric One‐Pot Synthesis of 1,4‐Dihydroquinolines via an Organocatalytic Aza‐Michael/Michael Cascade Strategy

AbstractA synthetic method for the construction of fully substituted enantioenriched 1,4‐dihydroquinolines using an organocatalytic aza‐Michael/Michael cascade reaction has been developed. The asymmetric reaction of 2‐(tosylamino)phenyl α,β‐unsaturated ketones with alkynyl aldehydes, promoted by diphenylprolinol O‐TMS ether as an organocatalyst, generated chiral 1,4‐dihydroquinolines in good to high yields with excellent enantioselectivities (up to 97 % ee).magnified image

Asymmetric synthesis of spiro[chroman-3,3′-pyrazol] scaffolds with an all-carbon quaternary stereocenter via a oxa-Michael–Michael cascade strategy with bifunctional amine-thiourea organocatalysts

The chiral spiro[chroman-3,3′-pyrazol] derivatives have been synthesized through a catalytic oxa-Michael–Michael cascade reaction of 2-hydroxynitrostyrenes with 4-alkenyl pyrazolin-3-ones in good yields with moderate to high stereoselectivities.

ChemInform Abstract: Organocatalytic Asymmetric Michael—Michael Cascade for the Construction of Highly Functionalized N‐Fused Piperidinoindoline Derivatives.

AbstractMichael—Michael cascade reaction of indole derivatives with nitroalkenes in the presence of cinchona derived bifunctional thiourea catalyst results in the formation of piperidinoindolines with moderate diastereoselectivities and excellent enantioselectivities.

ChemInform Abstract: A Highly Efficient and Green Cascade Synthesis of 3‐Methyl‐substituted‐4‐hydroxy‐1‐methyl‐quinolin‐2(1H)‐ones under Solvent‐ and Catalyst‐Free Conditions.

AbstractThe reaction proceeds via Knoevenagel—Michael cascade to yield symmetric products (III) and unsymmetric products (V).

ChemInform Abstract: Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.

AbstractThe diphenyl phosphinic acid‐catalyzed acetalization/oxa‐Michael cascade leads to formation of dioxolanes or oxazolidines in a diastereoselective fashion.

L-Proline-Grafted Mesoporous Silica with Alternating Hydrophobic and Hydrophilic Blocks to Promote Direct Asymmetric Aldol and Knoevenagel–Michael Cascade Reactions

Promotion of heterogeneous asymmetric catalysis is of major interest in the asymmetric catalysis field. In this work, a novel strategy for the synthesis of l-proline-grafted mesoporous silica with alternating hydrophobic and hydrophilic blocks to promote the heterogeneous asymmetric catalysis was reported. The surface synergies in the neat environment and the interface acceleration in aqueous medium thereby fostered high catalytic activities and enantioselectivity in the direct aldol reaction and the Knoevenagel–Michael cascade reaction. The l-proline loading could be reduced to as low as 0.63 mol %, giving 95% ee for anti-isomers and 81% ee for syn-isomers in the catalytic asymmetric aldol reaction of nitrobenzaldehyde and cyclohexanone, which was hard to accomplish on the homogeneous counterpart. In the direct asymmetric aldol reaction of ethyl-2-oxoacetate and cyclohexanone, 82% yield in 24 h and 90% ee were achieved. More exciting, the catalysts were applied to more exigent reactions. As an example, in the Knoevenagel–Michael cascade reaction, 85% yield in 10 h and up to 91% ee was achieved.

ChemInform Abstract: Facile Assembly of Chiral Tetrahydrothiopyrans Containing Four Consecutive Stereocenters via an Organocatalytic Enantioselective Michael—Michael Cascade.

AbstractSuitable reaction conditions are presented for the reaction of new bifunctional ketothioether enones with α,β‐unsaturated aldehydes to produce the title compounds with excellent enantioselectivities and only moderate diastereoselectivities.

ChemInform Abstract: An Organocatalytic Michael—Michael Cascade for the Enantioselective Construction of Spirocyclopentane Bioxindoles: Control of Four Contiguous Stereocenters.

ChemInformVolume 45, Issue 26 Heterocyclic Compounds ChemInform Abstract: An Organocatalytic Michael—Michael Cascade for the Enantioselective Construction of Spirocyclopentane Bioxindoles: Control of Four Contiguous Stereocenters. Wangsheng Sun, Wangsheng Sun Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorLiang Hong, Liang Hong Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorGongming Zhu, Gongming Zhu Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorZilong Wang, Zilong Wang Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorXiaojin Wei, Xiaojin Wei Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorJingman Ni, Jingman Ni Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorRui Wang, Rui Wang Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this author Wangsheng Sun, Wangsheng Sun Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorLiang Hong, Liang Hong Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorGongming Zhu, Gongming Zhu Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorZilong Wang, Zilong Wang Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorXiaojin Wei, Xiaojin Wei Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorJingman Ni, Jingman Ni Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this authorRui Wang, Rui Wang Sch. Life Sci., Lanzhou Univ., Lanzhou, Gansu 730000, Peop. Rep. ChinaSearch for more papers by this author First published: 12 June 2014 https://doi.org/10.1002/chin.201426104Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume45, Issue26July 1, 2014 RelatedInformation

Organocatalytic asymmetric Michael-Michael cascade for the construction of highly functionalized N-fused piperidinoindoline derivatives.

Application of indolin-3-one derivatives in a cascade reaction for efficient assembly of complex molecules is a much less explored research area. It is demonstrated that structurally interesting polysubstituted piperidino[1,2-a]indoline compounds containing four contiguous stereocenters including one tetrasubstituted carbon center can be readily obtained with good yields (up to 94% yield) and excellent enantioselectivities (up to >99% ee) by employing indolin-3-one derivatives as substrates via bifunctional catalysis.

“Amano” lipase DF-catalyzed efficient synthesis of 2,2′-arylmethylene dicyclohexane-1,3-dione derivatives in anhydrous media

A simple and efficient method was developed for the synthesis of 2,2′-arylmethylene dicyclohexane-1,3-dione derivatives via the Knoevenagel–Michael cascade reactions of aromatic aldehydes and 1,3-cyclic diketones catalyzed by “Amano” lipase DF, which expands the application field of enzyme catalytic promiscuity. This protocol provides several advantages over the traditional chemical synthesis, such as simple work-up procedure, high yields (up to 94%) and environmental friendliness.

Synthesis of Spiro[chroman/tetrahydrothiophene‐3,3′‐oxindole] ScaffoldsviaHeteroatom‐Michael–Michael Reactions: Easily Controlled EnantioselectivityviaBifunctional Catalysts

AbstractAn efficient method for the construction of chiral spirooxindole‐chroman and spirooxindole‐tetrahydrothiophene scaffolds with three consecutive chiral centers including an all‐carbon quaternary spirocenter has been developed. This method features an asymmetric thia/oxa‐Michael–Michael cascade sequence in a single operation in the presence of chiral tertiary amine‐thioureas as the catalysts, providing the desired products in good chemical yields and optical purities.magnified image

Facile Assembly of Chiral Tetrahydrothiopyrans Containing Four Consecutive Stereocenters via an Organocatalytic Enantioselective Michael–Michael Cascade

An organocatalytic enantioselective Michael-Michael cascade reaction has been implemented for the creation of structurally variant chiral tetrahydrothiopyrans. The process is realized by employment of new bifunctional ketothioether enones and proceeds highly enantioselectively with formation of four consecutive stereogenic centers.

ChemInform Abstract: Organocatalytic Oxa/Aza‐Michael—Michael Cascade Strategy for the Construction of Spiro [Chroman/Tetrahydroquinoline‐3,3′‐oxindole] Scaffolds.

AbstractUnder mild conditions, the newly developed procedure gives optically active products with excellent diastereoselectivities and enantioselectivities.

ChemInform Abstract: Organocatalyzed Michael—Michael Cascade Reaction: Asymmetric Synthesis of Polysubstituted Chromans.

AbstractThe title reaction provides a mild and efficient approach for the synthesis of the chiral benzopyrans (III) and (VI) with three consecutive stereocenters.