☆ 3.8 Review

Recent advances using cyclopropanols and cyclobutanols in ring-opening asymmetric synthesis

GREEN SYNTHESIS AND CATALYSIS (2022)

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Review Chemistry, Multidisciplinary

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Vincent Pirenne et al.

Summary: This review discusses the development of enantioselective methods for the ring opening of cyclopropanes, including reactions based on nonchiral cyclopropanes and asymmetric transformations of chiral substrates. It is organized according to substrate classes, focusing on both established and emerging methods for enantioselective ring opening reactions of different cyclopropanes.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt Homoenolates

Wei Huang et al.

Summary: The synthesis of multi-substituted cyclopropanes with high yields and enantioselectivity was achieved through the catalytic diastereo- and enantioselective hydroalkylation of 3,3-disubstituted cyclopropenes promoted by a chiral phosphine-cobalt complex. The approach allows for the direct introduction of functionalized alkyl groups onto the cyclopropane motif without the need for pre-formation of stoichiometric amounts of organometallic reagents, providing access to enantioenriched cyclopropanes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Selective Carbon-Carbon Bond Cleavage of Cyclopropanols

Tyler R. McDonald et al.

Summary: The carbon-carbon bond cleavage of cyclopropanols is a research hotspot, involving three main reactivity modes such as homoenolate chemistry, beta-keto radical chemistry, and acid-catalyzed ring-opening. Various methods for the C-C bond cleavage and functionalization of cyclopropanols are summarized, emphasizing their synthetic utility.

CHEMICAL REVIEWS (2021)

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Review Chemistry, Multidisciplinary

Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings

Masahiro Murakami et al.

Summary: This article reviews synthetic transformations involving the cleavage of a carbon-carbon bond of a four-membered ring from 2011 to 2019, with a particular focus on progress in catalytic reactions such as oxidative addition and beta-carbon elimination, as well as the increasing attention on beta-scission of radical intermediates. Additionally, Lewis acid-mediated and thermally induced ring-opening of cyclobutanone derivatives have garnered renewed interest, demonstrating the unique synthetic potentials of structurally strained four-membered ring compounds for constructing organic skeletons.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Cleavage of Cyclobutanols Through Ir-Catalyzed C-C Bond Activation: Mechanistic and Synthetic Aspects

Friederike Ratsch et al.

Summary: The Ir-catalyzed conversion of prochiral tert-cyclobutanols to beta-methyl-substituted ketones in toluene under mild conditions is effective for the enantioselective desymmetrization of substrates, yielding products with quaternary chirality centers with high ee values. The mechanistic differences compared to related Rh-I-catalyzed transformations were revealed through deuterium experiments and kinetic isotope effect measurements. The computational model proposed the initial formation of an Ir-III hydride intermediate and its subsequent beta-C elimination, allowing prediction of the stereochemical outcome.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Asymmetric Total Syntheses of Schizozygane Alkaloids

Wenqiang Zhou et al.

Summary: Through the development of a new method and key reactions, the concise, collective, and asymmetric total syntheses of four schizozygane alkaloids, including the first asymmetric synthesis, have been achieved in only 11-12 steps from tryptamines.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Palladium-Catalyzed Asymmetric Cross-Coupling Reactions of Cyclobutanols and Unactivated Olefins

Kangning Cao et al.

Summary: The study presents a highly selective Pd-catalyzed reaction for the synthesis of a series of chiral benzene-fused cyclic compounds in a convenient manner.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

Zhao Yang et al.

Summary: In this study, a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids has been achieved, starting from L-tryptophan and featuring a rigid cage scaffold. Two key bridged skeleton-forming reactions, the tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone alpha-allenylation, were utilized to assemble the caged sarpagine scaffold and install requisite derivative handles. This approach allowed for the total synthesis of five sarpagine alkaloids and three koumine alkaloids with various substituents and more complex cage scaffolds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate

Yoshiya Sekiguchi et al.

Summary: An enantioselective conjugate addition reaction using a zinc homoenolate catalytically generated from cyclopropanol and added to an alpha,beta-unsaturated ketone was reported. The reaction produced highly substituted cyclopentene derivatives with good to high enantioselectivities through intramolecular aldol condensation of 1,6-diketones. The use of a chiral amino alcohol as a ligand-accelerated the catalysis of the homoenolate generation and its conjugate addition.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Cobalt-catalyzed atom-economical, diastereo- and enantioselective coupling of aldimines and cyclopropanols

Zhikun Liang et al.

Summary: This method involves the catalytic generation of cobalt enolates from easily accessible cyclopropanols, followed by diastereo- and enantioselective additions to aldimines. The process leads to the formation of a wide range of beta-amino-ketones in high yields, with excellent diastereomeric and enantiomeric ratios, without the need for any stoichiometric amount of additives or reagents.

SCIENCE CHINA-CHEMISTRY (2021)

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Article Chemistry, Physical

Pd-Catalyzed Ring-Closing/Ring-Opening Cross Coupling Reactions: Enantioselective Diarylation of Unactivated Olefins

Lantao Liu et al.

Summary: A Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates. This method provides a convenient approach to chiral 2,3-dihydrobenzofurans with excellent enantioselectivities, and has been applied in the concise synthesis of analogues of cannabinoid receptor 2 agonists.

ACS CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Recent development and applications of semipinacol rearrangement reactions

Xiao-Ming Zhang et al.

Summary: Semipinacol rearrangement plays a crucial role in organic synthesis, and the development of novel rearrangement reactions has been a vibrant topic that continues to shape the research field. Recent breakthroughs in new electrophiles, tandem processes, and enantioselective catalytic transformations have further enriched the toolbox in this field.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol

Jie Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Applied

Enantioselective Copper-Catalyzed Radical Ring-Opening Cyanation of Cyclopropanols and Cyclopropanone Acetals

Lianqian Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins

Paul R. Leger et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (-)-Suaveoline

Qiuyuan Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Total Synthesis of α-Tocopherol through Enantioselective Iridium-Catalyzed Fragmentation of a Spiro-Cyclobutanol Intermediate

Friederike Ratsch et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

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Article Chemistry, Physical

Cobalt-Catalyzed Enantioselective and Chemodivergent Addition of Cyclopropanols to Oxabicyclic Alkenes

Junfeng Yang et al.

ACS CATALYSIS (2019)

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Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis

Kaining Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C-C bond scission

Dongping Wang et al.

CHEMICAL SCIENCE (2018)

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Review Chemistry, Multidisciplinary

Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Cyclobutanone via Lewis Acid Catalyzed Tandem Cyclopropanation/Semipinacol Rearrangement

Su Yong Shim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Organic

BINOL-phosphoric acids-catalyzed furylogous pinacol rearrangement of 1-[5-(hydroxy-diaryl-methyl)-furan-2-yl]-cyclobutanols into spiro cyclopentanones

Chengcheng Fei et al.

TETRAHEDRON (2018)

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Article Chemistry, Multidisciplinary

Enantioselective Photochemical Organocascade Catalysis

Lukasz Wozniak et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Review Chemistry, Multidisciplinary

Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

Gabriele Fumagalli et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Multidisciplinary

Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds

Hatice G. Yayla et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Review Chemistry, Multidisciplinary

Tuning Reactivity and Selectivity in Hydrogen Atom Transfer from Aliphatic C-H Bonds to Alkoxyl Radicals: Role of Structural and Medium Effects

Michela Salamone et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Article Chemistry, Multidisciplinary

Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by C-C Bond Cleavage

Rongguo Ren et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ-Fluorinated Ketones

Huijun Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Enantioselective Insertion of a Carbenoid Carbon into a C-C Bond To Expand Cyclobutanols to Cyclopentanols

Akira Yada et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Exploitation of Rh(I)-Rh(III) cycles in enantioselective C-C bond cleavages: access to beta-tetralones and benzobicyclo[2.2.2]octanones

Laetitia Souillart et al.

CHEMICAL SCIENCE (2014)

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Article Chemistry, Multidisciplinary

Reactivity Change of Cyclobutanols towards Isocyanates: Rhodium Favors C-Carbamoylation over O-Carbamoylation

Naoki Ishida et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Rhodium-Catalyzed C-C Bond Cleavage: Construction of Acyclic Methyl Substituted Quaternary Stereogenic Centers

Tobias Seiser et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Asymmetric synthesis of 3,4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones

Takanori Matsuda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Organic

Enantioselective C-C bond cleavage creating chiral quaternary carbon centers

Takanori Matsuda et al.

ORGANIC LETTERS (2006)

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Review Chemistry, Multidisciplinary

The chemistry of cyclopropanols

OG Kulinkovich

CHEMICAL REVIEWS (2003)

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