Lewis base catalyzed allylation reaction of N-aryl amides with Morita–Baylis–Hillman carbonates

Wang, Shutao; Yong-liang, Gao; Song, Shaoli; Li, Xinze; Zhang, Zhuoqi; Xiang, Jinbao; Zheng, Lianyou

doi:10.1016/j.tet.2022.132903

Cited by 4 publications

(2 citation statements)

References 51 publications

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“…Typically, these reactions were promoted by nucleophilic catalysts such as tertiary amines or phosphines. A variety of reactive C(sp 3 ) nucleophiles have been reported to undergo allylation reaction with MBH carbonates . The α-allylation reactions of several electron-deficient cyclic imines such as cyclic N -sulfonylimines and sulfamidate imines with isatin-derived MBH carbonates under the catalysis of Lewis bases have been reported by Chen and Samanta groups, respectively (Scheme c) .…”

Section: Introductionmentioning

confidence: 99%

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Wang

Zhang

et al. 2023

J. Org. Chem.

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In this work, a mild and efficient catalyst-free α-allylation of 3,4-dihydroisoquinoline imines with Morita−Baylis− Hillman (MBH) carbonates was reported. The scopes of 3,4-dihydroisoquinolines and MBH carbonates as well as gram-scale synthesis were investigated, and densely functionalized adducts were obtained in moderate to good yields. The synthetic utility of these versatile synthons was further demonstrated by the facile synthesis of diverse benzo[a]quinolizidine skeletons.

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Section: Introductionmentioning

confidence: 99%

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Wang

Zhang

et al. 2023

J. Org. Chem.

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“…MBH adducts contain the structural moieties of allylic alcohols or amines, Michael acceptors, and electron-withdrawing groups, which makes them valuable substrates for various types of reactions such as Michael addition, allylic substitution, cycloaddition reaction, Friedel-Crafts reaction, Claisen rearrangement, etc. [ 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ]. Based on our previous studies of 1,3-dipolar cycloaddition, Michael addition of azomethine ylides and azomethine imines and palladium-catalyzed tandem reaction to construct 3,3-disubstituted indolinones [ 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ], herein we report the mono-/diallylation of isatin N , N ′-cyclic azomethine imines from the condensation of isatin and pyrazolidones with MBH carbonates.…”

Section: Introductionmentioning

confidence: 99%

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Wang

Li²,

Yang

et al. 2023

Molecules

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Allylation of N-unsubstituted isatin N,N′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave N-allylated and N, β-diallylated isatin N,N′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.

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Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

Nosovska,

Liebing,

Vilotijevic

2024

Chemistry A European J

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Trifluoro‐ and trichloroacetamides serving as pronucleophiles undergo enantioselective Lewis base catalyzed N‐allylation with Morita‐Baylis‐Hillman carbonates to produce enantioenriched β‐amino acid derivatives. The reactions proceed as a kinetic resolution to give the allylation products and the remaining carbonates in good yields and high enantioselectivity. The obtained products are amenable to diastereoselective derivatization to produce a library of spiro‐isoxazoline lactams.

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Lewis base catalyzed allylation reaction of N-aryl amides with Morita–Baylis–Hillman carbonates

Cited by 4 publications

References 51 publications

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Synthesis of β‐Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N‐Allylation of Halogenated Amides with Morita‐Baylis‐Hillman Carbonates

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