Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

Rueping, Magnus; Moreth, Stefan A.; Bolte, Michael

doi:10.5560/znb.2012-0183

Cited by 16 publications

(10 citation statements)

References 14 publications

(15 reference statements)

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“…[20] In 2012, Rueping reported the synthesis of 2,3-dihydroquinolinones 13 starting from N-benzyl and N-allyl anilines 14. [21] In this case, chiral BPA-derived triflimide VIII was the catalyst of choice, giving rise to the final products in good yields but low enantioselectivities (50-63 % ee) (Scheme 6, C). Later on, Yu found that acetamides could perform as good nucleophilic nitrogen source by using chiral thioureas as the organocatalysts.…”

Section: Enones As Michael Acceptorsmentioning

confidence: 99%

Two Decades of Progress in the Asymmetric Intramolecular aza‐Michael Reaction

Sánchez‐Roselló

Escolano

Gaviña

et al. 2021

The Chemical Record

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The asymmetric intramolecular aza-Michael reaction (IMAMR) is a very convenient strategy for the generation of heterocycles bearing nitrogen-substituted stereocenters. Due to the ubiquitous presence of these skeletons in natural products, the IMAMR has found widespread applications in the total synthesis of alkaloids and biologically relevant compounds. The development of asymmetric versions of the IMAMR are quite recent, most of them reported in this century. The fundamental advances in this field involve the use of organocatalysts. Chiral imidazolidinones, diaryl prolinol derivatives, Cinchone-derived primary amines and quaternary ammonium salts, and BINOL-derived phosphoric acids account for the success of those methodologies. Moreover, the use of N-sulfinyl imines with a dual role, as nitrogen nucleophiles and as chiral auxiliaries, appeared as a versatile mode of performing the asymmetric IMAMR.

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Section: Enones As Michael Acceptorsmentioning

confidence: 99%

Two Decades of Progress in the Asymmetric Intramolecular aza‐Michael Reaction

Sánchez‐Roselló

Escolano

Gaviña

et al. 2021

The Chemical Record

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“…In 2012, Rueping et al reported a new synthetic route for preparing N-allyland N-benzyl-protected 2-aryl-substituted dihydroquinones 58 undergoing an enantioselective Brønsted-acid-catalyzed intramolecular Michael addition mechanism (Scheme 53). 102 Dihydroquinolones 58 were obtained with N-allyl or N-benzyl anilines substituted with a chalcone moiety in the ortho position as starting materials in the presence of chiral BINOL-based N-triflyl phosphor-amides (BTPA) in dimethyl glycol at room temperature. X-ray crystal structure analysis proved that the absolute configuration of product was the S form.…”

Section: Asymmetric Nucleophilic Addition Reactionsmentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of 4-Quinolones

Shen

Wang

Zhang

et al. 2019

Chem

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The 4-quinolones and their analogs are a heterogeneous group of biologically active compounds that have evolved in modern days to provide utilities at the forefront of antibiotic research. They have been used to combat Gram-negative or Gram-positive bacteria, suppress tumor growth, and treat many serious infections. These antimicrobial agents have also been used to promote apoptosis and DNA repair for the treatment of cancer. This review summarizes the experimental progress made in the synthetic development of various catalytic routes to preparing 4-quinolones and their analogs; discusses our current understanding of the reaction mechanisms involving biocatalytic synthesis, general catalytic synthesis, and asymmetric synthesis; and finally presents the future prospects of the emerging field.

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“…Starting from N-allyl or N-benzyl anilines 22 substituted with a chalcone moiety in the ortho position, cyclisation in the presence of chiral N-trifyl binolphosphoramide XI in dimethyl glycol at room temperature afforded dihydroquinolones 23 in moderate to very good yields and with moderate enantioselectivities (Scheme 13). 35 Scheme 9 The commonly accepted mechanism of the IMAMR with enones catalysed by 9-amino-9-deoxy-epi-hydroquinine.…”

Section: Conjugated Ketones As Michael Acceptorsmentioning

confidence: 99%

A general overview of the organocatalytic intramolecular aza-Michael reaction

et al. 2014

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The organocatalytic intramolecular aza-Michael reaction gives access to enantiomerically enriched nitrogen-containing heterocycles in a very simple manner. Enals, enones, conjugated esters and nitro olefins have been employed as Michael acceptors, while moderate nitrogen nucleophiles such as sulphonamides, carbamates and amides have been shown to be appropriate Michael donors in this type of reaction. Additionally, the process has been performed under both covalent and non-covalent catalysis, with diaryl prolinols, imidazolidinones, thioureas and chiral binol phosphoric acids being the most frequently used catalysts. The level of efficiency reached with this protocol is demonstrated by the implementation of numerous tandem processes, as well as the total synthesis of several natural products.

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Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

Cited by 16 publications

References 14 publications

Two Decades of Progress in the Asymmetric Intramolecular aza‐Michael Reaction

Two Decades of Progress in the Asymmetric Intramolecular aza‐Michael Reaction

Recent Advances in the Catalytic Synthesis of 4-Quinolones

A general overview of the organocatalytic intramolecular aza-Michael reaction

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