Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides

Ray, Bidisha; Mukherjee, Santanu

doi:10.1016/j.tet.2019.04.049

Cited by 12 publications

(6 citation statements)

References 86 publications

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“…These adducts exhibit consecutive tertiary and all‐carbon quaternary steroecenters and are obtained in good yield, moderate diastereoselectivity and good to excellent enantioselectivity (Scheme 63). [116] However, N ‐alkyl maleimides and ortho ‐substituted N ‐aryl maleimides were completely unreactive under these conditions.…”

Section: Squaramide‐based Multifunctional Brønsted Base Catalystsmentioning

confidence: 97%

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Progress in (Thio)urea‐ and Squaramide‐Based Brønsted Base Catalysts with Multiple H‐Bond Donors

et al. 2023

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Thiourea‐ and squaramide‐based bifunctional base catalysts represent nowadays a powerful tool in the field of asymmetric catalysis and have demonstrated very efficient for promoting a wide variety of transformations enantioselectively. New versions that incorporate one or various additional H‐bond donor site(s) in the catalyst structure have been developed recently which led to more active (reduced catalyst loadings) and selective catalysts. This review highlights the pioneering ideas and the most recent contributions to the area with the material organized according to the nature of the additional H‐bond donor functionality. The advantages, current limitations and perspectives of these new multifunctional catalysts are discussed.

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Section: Squaramide‐based Multifunctional Brønsted Base Catalystsmentioning

confidence: 97%

“…Michael addition reaction of deconjugated butyrolactams to Narylmaleimides, Mukherjee, 2019. [116] Scheme 64. Amide-squaramide iminophosphorane BBs C92 and C93 as promoters of: a) Intramolecular aza-Michael reaction of urea linked α,βunsaturated esters.…”

Section: Squaramide-amide Systemsmentioning

confidence: 99%

Progress in (Thio)urea‐ and Squaramide‐Based Brønsted Base Catalysts with Multiple H‐Bond Donors

et al. 2023

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“…The next year, this group extended the Michael acceptor to maleimides 362 (Table 5). 98 With bifunctional tertiary aminosquaramide C44 as the catalyst, the α-selective Michael addition was smoothly implemented, leading to the formation of densely functionalized products 363 in 65-75% yields with 2 : 1-3 : 1 dr, and 90-98% ee values.…”

Section: Unsaturated Butyrolactamsmentioning

confidence: 99%

Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

et al. 2023

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“…Mukherjee and Ray have reported an unprecedented asymmetric 1,4-addition of deconjugated butyrolactams 144 to N -arylmalemides 145 using the bifunctional squaramide catalyst 3K (Scheme 48 ). 96 The Michael adducts 146 were generated with high yields and excellent enantioselectivities. Unlike deconjugated butenolides, butyrolactams prefer attack at the α-position.…”

Section: Hydrogen-bonding Catalysismentioning

confidence: 99%

Unravelling the Development of Non-Covalent Organocatalysis in India

Sahoo¹,

Panda²,

Sahoo³

2022

Synlett

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This review is devoted to underpinning the contributions of Indian researchers towards asymmetric organocatalysis. More specifically, a comprehensive compilation of reactions mediated by a wide range of non-covalent catalysis is illustrated. A detailed overview of vividly catalogued asymmetric organic transformations promoted by hydrogen bonding and Brønsted acid catalysis, alongside an assortment of catalysts is provided. Although asymmetric organocatalysis has etched itself in history, we aim to showcase the scientific metamorphosis of Indian research from baby steps to large strides within this field. 1 Introduction2 Non-Covalent Catalysis and Its Various Activation Modes3 Hydrogen-Bonding Catalysis3.1 Urea- and Thiourea-Derived Organocatalysts3.1.1 Thiourea-Derived Organocatalysts3.1.2 Urea-Derived Organocatalysts3.2 Squaramide-Derived Organocatalysts3.2.1 Michael Reactions3.2.2 C-Alkylation Reactions3.2.3 Mannich Reactions3.2.4 [3+2] Cycloaddition Reactions3.3 Cinchona-Alkaloid-Derived Organocatalysts3.3.1 Michael Reactions3.3.2 Aldol Reactions3.3.3 Friedel–Crafts Reactions3.3.4 Vinylogous Alkylation of 4-Methylcoumarins3.3.5 C-Sulfenylation Reactions3.3.6 Peroxyhemiacetalisation of Isochromans3.3.7 Diels–Alder Reactions3.3.8 Cycloaddition Reactions3.3.9 Morita–Baylis–Hilman Reactions4 Brønsted Acid Derived Organocatalysts4.1 Chiral Phosphoric Acid Catalysis4.1.1 Diels–Alder Reactions4.1.2 Addition of Ketimines4.1.3 Annulation of Acyclic Enecarbamates5 Conclusion

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Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides

Cited by 12 publications

References 86 publications

Progress in (Thio)urea‐ and Squaramide‐Based Brønsted Base Catalysts with Multiple H‐Bond Donors

Progress in (Thio)urea‐ and Squaramide‐Based Brønsted Base Catalysts with Multiple H‐Bond Donors

Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

Unravelling the Development of Non-Covalent Organocatalysis in India

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