The synthesis and use of γ-chloro-enamides for the subsequent construction of novel enamide-containing small molecules

Golliher, Alexandra E.; Tenorio, Antonio J.; Cornali, Brandon M.; Monroy, Erika Y.; Tello‐Aburto, Rodolfo; Holguín, F. Omar; Maio, William A.

doi:10.1016/j.tet.2021.132536

Cited by 3 publications

(2 citation statements)

References 52 publications

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“…19 A single example of a DA reaction involving a linear conjugated triene-tertiaryenamide, namely, N-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)pyrrolidin-2-one, was reported by Maio; the amide derivative was found to undergo cycloaddition with maleic anhydride under thermal conditions. 20 Interestingly, an opposite regioselectivity was observed when compared with Jørgensen's works 12,13a and only the internal diene reacted to afford the racemic endo-product (Scheme 1c). Motivated from this precedent along with our previous work on diene-controlled regiodivergent (4 + 2) cycloaddition, 21 we envisioned that the regioselectivity might be influenced by the nature of the substituent on the triene.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Thus far, the linear N H-1,3,5-triene-1-carbamates (RNHCOOR′) have found limited use despite their potential to undergo diverse cycloadditions around of each unsaturation for the synthesis of advanced compounds . A single example of a DA reaction involving a linear conjugated triene-tertiary-enamide, namely, N -((1 E ,3 E )-4-phenylbuta-1,3-dien-1-yl)pyrrolidin-2-one, was reported by Maio; the amide derivative was found to undergo cycloaddition with maleic anhydride under thermal conditions . Interestingly, an opposite regioselectivity was observed when compared with Jørgensen’s works , and only the internal diene reacted to afford the racemic endo -product (Scheme c).…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis

Naulin,

Lombard,

Gandon

et al. 2023

J. Am. Chem. Soc.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis

Naulin,

Lombard,

Gandon

et al. 2023

J. Am. Chem. Soc.

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Regioselective Carbozincation and Further Functionalization of Allenamides Catalyzed by an N‐Heterocyclic Carbene (NHC)‐Copper Complex

Takimoto,

Hou

2023

Asian J Org Chem

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An efficient protocol for the carbozincation of allenamides with dialkylzinc reagents catalyzed by an NHC‐Cu complex has been developed. This protocol could provide alkenylzinc species introducing the alkyl group to γ‐position and the zinc component to β‐position of the allenamides in a regio‐ and stereoselective manner. The resulting alkenylzinc species can undergo further C‐C bond‐forming reactions, such as allylation, arylation, and benzoylation, affording a variety of β,β‐disubstituted enamides with well‐controlled configurations of the two substituents. Moreover, the chiral allenamide synthesized via this method can be converted to a chiral aminocyclopropane derivative. In view of the high regio‐ and stereoselectivity and the convenient one‐pot procedure, this sequential transformation protocol offers a potentially useful method for synthesizing multi‐substituted enamides, which are important compounds in synthetic organic chemistry.

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Exploring the reactivity of (hetero)aryl amides in the Chan‐Evans‐Lam reaction with arylalkenyl boron reagents

Ferreira,

Guerreiro,

Santos

et al. 2024

Eur J Org Chem

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The unique reactivity and stability of enamides make them attractive reagents in organic synthesis. Herein, we investigated the reactivity of acetanilides and pyridyl acetamides in the formation of a C–N bond through a Chan‐Evans‐Lam reaction using arylalkenyl boron‐based reagents yielding a wide scope of N‐aryl enamides with an E configuration. The products obtained have been applied in the synthesis of N‐heterocycles, an important scaffold in several biologically active compounds, via sequential Heck reaction to prove the practical utility of the prepared N‐aryl enamides.

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The synthesis and use of γ-chloro-enamides for the subsequent construction of novel enamide-containing small molecules

Cited by 3 publications

References 52 publications

Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis

Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis

Regioselective Carbozincation and Further Functionalization of Allenamides Catalyzed by an N‐Heterocyclic Carbene (NHC)‐Copper Complex

Exploring the reactivity of (hetero)aryl amides in the Chan‐Evans‐Lam reaction with arylalkenyl boron reagents

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