Desymmetric hydrogenation of a meso-cyclic acid anhydride toward biotin synthesis

Yoshimura, Masahiro; Tsuda, Kazuomi; Nakatsuka, Hiroshi; Yamamura, Takuya; Kitamura, Masato

doi:10.1016/j.tet.2011.09.065

Cited by 14 publications

(5 citation statements)

References 38 publications

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“…The chiral product with up to 51% ee is reported in a patent . Recently, using chiral Ru catalysts bearing chiral bidentate ligands under conditions described in Lyons’s report (vide supra), Kitamura reported highly chemoselective formation of the d -lactone relevant for biotin production (S/C = 2000), however, with a moderate enantiomeric excess, although in almost quantitative yield …”

Section: Molecular Hydrogen Activation On Transition Metal Complexesmentioning

confidence: 99%

Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen

2012

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A comprehensive overview on homogeneous catalytic hydrogenation of carboxylic acids and its derivatives as well as carbonic acid derivatives with transition metal-based molecular catalysts is described. Despite the tremendous potential in the hydrogenation of these less electrophilic carbonyl compounds using molecular hydrogen in synthetic organic chemistry, their reduction still relies mostly on the stoichiometric use of metal hydride reagents, such as LiAlH 4 , NaBH 4 , and their derivatives. For the past decade, a significant and rapid progress in particularly ester hydrogenation has been achieved by utilization of conceptually new bifunctional molecular catalysts originating from the metal−ligand cooperation effects. The bifunctional-catalyst-promoted hydrogenation using molecular hydrogen is now realized to be a practical tool in synthetic organic chemistry in both academia and industry. The industrial outlook for the present hydrogenation is bright because of its operational simplicity, scope, economic viability, and growing awareness of the need for green chemistry.

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Section: Molecular Hydrogen Activation On Transition Metal Complexesmentioning

confidence: 99%

Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen

2012

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Section: Assembly Of the Lactone Core Structurementioning

confidence: 99%

“…The utility of this method has been illustrated by Krohn and Riaz with the total synthesis of (+)-xyloketal D. 276 Moreover, Ru-catalyzed hydrogenation of a meso-cyclic acid anhydride was successfully established by Kitamura et al to obtain enantiomerically enriched γ-butyrolactones by using a chiral phosphine ligand. 277 Catalytic asymmetric hydrogenation of γ-keto esters is another common approach toward the synthesis of γ-butyrolactones. 278−282 A few methods, such as transition metal catalyzed hydrogenation, 283,284 and related hydrosilylation 285 and hydroboration, 286 have been applied to perform this type of reaction.…”

Section: Asymmetric Hydrogenationmentioning

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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“…For example, Kitamura et al achieved Ru-catalyzed desymmetric hydrogenation of a meso-cyclic acid anhydride 174 to obtain enantiomerically enriched γ-lactone 175 (Scheme 71) [119]. Some approaches on the basis of the desymmetrization concept have been published.…”

Section: γ-Lactone Synthesis Based On Desymmetrization Reactionsmentioning

confidence: 99%

Green and Catalytic Methods for γ-Lactone Synthesis

Yanai

2015

Green Synthetic Approaches for Biologically Relevant Heterocycles

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Desymmetric hydrogenation of a meso-cyclic acid anhydride toward biotin synthesis

Cited by 14 publications

References 38 publications

Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen

Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

Green and Catalytic Methods for γ-Lactone Synthesis

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