Green and Catalytic Methods for γ-Lactone Synthesis

Yanai, Hikaru

doi:10.1016/b978-0-12-800070-0.00010-4

Cited by 14 publications

(4 citation statements)

References 171 publications

(77 reference statements)

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“…The five-membered cyclic ester, the essential framework of γ-butenolide and γ-butyrolactone, constitutes the structural core shared by numerous natural products. − γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, display an impressive range of biological activities which are important for the development of physiological and therapeutic agents . Some representative members of this family are depicted in Figure .…”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

2017

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γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials.

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Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

2017

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“…As depicted in Scheme 1b, a number of efficient methods were established in the past few decades. 2,3 Among them, the vinylogous addition reactions of dihydro-furanones and silyloxyfurans, including vinylogous Michael, aldol, Mannich, Morita–Baylis–Hillman (MBH) and allylic substitution reactions, represent a facile route to structurally diverse enantioenriched γ-butenolide derivatives. 2,4 In addition, the Feringa group reported the enantioselective synthesis of optically active γ-butenolides via chiral copper-catalyzed hetero-allylic asymmetric alkylation (h-AAA) and ruthenium-catalyzed RCM tandem reactions.…”

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confidence: 99%

Concise synthesis of chiral γ-butenolides via an allylation/lactonization cascade reaction

Tan,

Yihuo,

et al. 2024

Chem. Commun.

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“…Endowed with the advantages of sustainability, cost, time effectiveness, step economy, and low waste production, one-pot operation provides efficient pathways for the execution of multiple transformations involving the formation of multiple C–C and/or C–X bonds . Owing to the numerous advantages, asymmetric one-pot reactions have been frequently utilized in manufacturing small to complex chiral molecules including heterocycles …”

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confidence: 99%

Asymmetric Multifunctional Modular Organocatalysis: One-Pot Direct Strategy to Enantiopure α,β-Disubstituted γ-Butyrolactones

et al. 2019

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A simple and efficient approach to enantioenriched α,β-disubstituted γ-butyrolactones has been developed through multifunctional modular organocatalysis in a highly enantioselective (>99% ee) and diastereoselective (>30:1) manner following a one-pot sequential Michael−hemiacetalization−oxidation reaction. The catalytic process has great substrate compatibility, and the products have been transformed to synthetically useful molecules. The methodology has also been applied to the formal synthesis of (+)-Pilocarpine.

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Green and Catalytic Methods for γ-Lactone Synthesis

Cited by 14 publications

References 171 publications

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

Concise synthesis of chiral γ-butenolides via an allylation/lactonization cascade reaction

Asymmetric Multifunctional Modular Organocatalysis: One-Pot Direct Strategy to Enantiopure α,β-Disubstituted γ-Butyrolactones

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