4.4 Review

Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis

Wu-Lin Yang et al.

Summary: The enantioselective cascade reaction between racemic 2-(1-hydroxyallyl)phenols and alkynols/alkynamides was achieved using a gold and iridium sequential catalytic system. This method provides efficient access to spiroketals and spiroaminals with excellent enantioselectivities. The synthetic utility of this method has been demonstrated by the enantioselective synthesis of an analogue of Paecilospirone.

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Chiral Squaramide Catalyzed Asymmetric Spiroketalization toward Aromatic [6,5] Spiroketals

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Summary: An efficient enantio- and diastereoselective spiroketalization method of aromatic ketone tethered to ortho-homoformyl and enone moiety via in situ enol formation using quinine derived squaramide organocatalyst is disclosed. This method provides access to aromatic [6,5] spiroketals with complete atom economy. Furthermore, the aromatic spiroketals can undergo Bronsted acid catalyzed Piancatelli type rearrangement to afford dihydronaphtho[1,2-b]furans with retention of enantioselectivities.

ORGANIC LETTERS (2022)

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Organocatalytic Enantioselective Construction of Spiroketal Lactones Bearing Axial and Central Chirality via an Asymmetric Domino Reaction

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Summary: This paper proposes a novel strategy for the asymmetric synthesis of chiral compounds with multiple stereogenic elements via a single catalyst. The method successfully synthesizes spiroketal lactones with excellent yields and enantioselectivity.

ORGANIC LETTERS (2022)

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A Type of Structurally Adaptable Aromatic Spiroketal Based Chiral Diphosphine Ligands in Asymmetric Catalysis

Xiaoming Wang et al.

Summary: The research group developed an efficient synthesis of chiral aromatic spiroketals and corresponding diphosphine ligands, which exhibit unique adaptable structures and outstanding catalytic performance in transition metal complexes. The SKP ligands have shown remarkable versatility in coordinating with various transition metals and have demonstrated excellent efficiency in challenging asymmetric transformations, indicating their potential in advancing asymmetric catalysis.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

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Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade

Kimberly M. Hilby et al.

Summary: A Lewis base catalyzed, enantioselective sulfenocyclization of alkenes to afford [6,6]spiroketals has been developed with excellent yields and enantioselectivities. The method allows for rapid formation of highly substituted spiroketals using a chiral Lewis base catalyst and electrophilic sulfur source.

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Diastereo- and Enantioselective Synthesis of Eight-Membered Heterocycles via an Allylation/Ring Expansion Sequence Enabled by Multiple Catalysis

Wu-Lin Yang et al.

Summary: This study developed an efficient method for synthesizing 8-membered benzo[b]oxocines with high stereocontrol and yield through a sequential catalytic reaction. The chiral iridium catalyst was found to control enantioselectivity, while the chiral bifunctional squaramide catalyst controlled diastereoselectivity. The strategy was also demonstrated to be applicable for synthesizing other nitrogen heterocycles with high enantiomeric enrichment.

ACS CATALYSIS (2021)

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Enantioselective Catalytic Cyclopropanation-Rearrangement Approach to Chiral Spiroketals

Kuioyng Dong et al.

Summary: A highly enantioselective synthesis of chiral heterobicyclic spiroketals is reported using a one-pot cyclopropanation-rearrangement cascade reaction catalyzed by a chiral Rh(II) catalyst and tetrabutylammonium fluoride (TBAF). Exocyclic vinyl substrates react with tert-butyldimethylsilyl-protected enoldiazoacetates to form spirocyclopropanes under chiral dirhodium(II) carboxylates catalysis, followed by desilylation and rearrangement in the presence of TBAF to yield (S)-spiroketals with high yields and excellent chirality retention (>95% ee).

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Application of Cascade Reactions in the Synthesis of Sprio-heterocycles Initiated by Intramolecular Cyclization of Alkynols

Shuyan Yu et al.

Summary: This paper reviews the application progress of cascade reactions initiated by intramolecular cyclization of alkynols in the synthesis of spiro-heterocycles, aiming to highlight efficient methods for constructing these compounds. The analysis is based on the different atom numbers of substrates involved in building the spiro frameworks, describing catalytic systems, reaction mechanisms, challenges, and future directions in this field.

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Tianyu Zheng et al.

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Bimetallic Catalytic Asymmetric Tandem Reaction of β-Alkynyl Ketones to Synthesize 6,6-Spiroketals

Shulin Ge et al.

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Enantioselective Synthesis of Cyclohexadienone Containing Spiroketals via DyKat Ketalization/oxa-Michael Addition Cascade

Reddy Rajasekhar Reddy et al.

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Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

Alonso J. Arguelles et al.

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Making Spiroketal-based Diphosphine (SKP) Ligands via a Catalytic Asymmetric Approach

Xiaoming Wang et al.

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ERecent progress in the isolation, bioactivity, biosynthesis, and total synthesis of natural spiroketals

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Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex

James Y. Hamilton et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Total Synthesis and Stereochemical Assignment of (+)-Broussonetine H

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Synthesis of Spiroketals by Synergistic Gold and Scandium Catalysis

Man Liang et al.

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Synergistic silver/scandium catalysis for divergent synthesis of skeletally diverse chromene derivatives

Shuai Liu et al.

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Designed Spiroketal Protein Modulation

Marcel Scheepstra et al.

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Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions

Yaroslav Ya. Khomutnyk et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts

Naoki Yoneda et al.

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Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products

Darcy J. Atkinson et al.

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Spiroacetal Formation through Telescoped Cycloaddition and Carbon-Hydrogen Bond Functionalization: Total Synthesis of Bistramide A

Xun Han et al.

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Synthesis of Spiroaminals and Spiroketals with Bimetallic Relay Catalysis

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A catalytic multicomponent coupling reaction for the enantioselective synthesis of spiroacetals

Lara Cala et al.

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Simple, but Challenging: Recent Developments in the Asymmetric Synthesis of Spiroketals

Michael Wilsdorf et al.

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Chiral Phosphoric Acid-Catalyzed Enantioselective and Diastereoselective Spiroketalizations

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Asymmetric spiroacetalization catalysed by confined Bronsted acids

Ilija Coric et al.

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Strategies for Spiroketal Synthesis Based on Transition-Metal Catalysis

Jean A. Palmes et al.

SYNTHESIS-STUTTGART (2012)

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Total Synthesis of Paecilospirone

Tsz-Ying Yuen et al.

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Isolation, biological activity and synthesis of benzannulated spiroketal natural products

Jonathan Sperry et al.

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Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction

Jonathan Sperry et al.

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Spiro Skeletons: A Class of Privileged Structure for Chiral Ligand Design

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The hetero-Diels-Alder approach to spiroketals

Mark A. Rizzacasa et al.

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Asymmetric synthesis of naturally occuring spiroketals

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An alkyne strategy for the asymmetric synthesis of natural products: Application to (+)-spirolaxine methyl ether

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Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile

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Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies

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Five new chromones possessing monoamine oxidase inhibitory activity from an Ascomycete, Chaetomium quadrangulatum

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