4.8 Article

Zinc-Catalyzed β-Functionalization of Cyclopropanols via Enolized Homoenolate

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
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)

Review Chemistry, Multidisciplinary

Metal-Catalyzed Transformations of Cyclopropanols via Homoenolates

Yoshiya Sekiguchi et al.

Summary: This review article provides an overview of the development of homoenolate transformations, highlighting the reliable use of siloxycyclopropanes as precursors and the attractive alternative of unprotected cyclopropanols, often catalytically generated, in carbon-carbon and carbon-heteroatom bond-forming reactions. The transformations are classified based on the metals involved in the cyclopropane ring opening.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2021)

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)

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)

Article Chemistry, Organic

Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

Yoshiya Sekiguchi et al.

Summary: This work presents a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates under mild and neutral conditions, showing good yields and linear selectivity. Mechanistic experiments support a catalytic cycle involving several key steps including decarboxylative oxidative addition and C-C reductive elimination.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones

Xinpei Cai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Asymmetric Photocatalysis by Intramolecular Hydrogen-Atom Transfer in Photoexcited Catalyst-Substrate Complex

Chenhao Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Michael S. West et al.

ORGANIC LETTERS (2019)

Article Chemistry, Organic

Total syntheses via cyclopropanols

Xinpei Cai et al.

TETRAHEDRON (2019)

Article Chemistry, Multidisciplinary

Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis

Junfeng Yang et al.

CHEMICAL SCIENCE (2018)

Article Chemistry, Multidisciplinary

Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines

L. Reginald Mills et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols

Dexter C. Davis et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Organic

Transition-Metal-Catalyzed C-C and C-X Bond-Forming Reactions Using Cyclopropanols

Andrei Nikolaev et al.

SYNTHESIS-STUTTGART (2016)

Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Multidisciplinary

On the Mechanism of N-Heterocyclic Carbene-Catalyzed Reactions Involving Acyl Azoliums

Jessada Mahatthananchai et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Review Chemistry, Multidisciplinary

A New Golden Age for Donor-Acceptor Cyclopropanes

Tobias F. Schneider et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Review Multidisciplinary Sciences

An overview of N-heterocyclic carbenes

Matthew N. Hopkinson et al.

NATURE (2014)

Article Chemistry, Multidisciplinary

SN2′ Alkylation of Cyclopropanols via Homoenolates

Pragna Pratic Das et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Efficient synthesis of polysubstituted isochromanones via a novel photochemical rearrangement

Wujiong Xia et al.

CHEMICAL COMMUNICATIONS (2011)

Review Chemistry, Multidisciplinary

Organocatalysis by N-heterocyclic, carbenes

Dieter Enders et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Transition metal chemistry of cyclopropenes and cyclopropanes

Michael Rubin et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

N-heterocyclic carbenes as organocatalysts

Nicolas Marion et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Chemistry, Multidisciplinary

Generation of β-keto radicals from cyclopropanols catalyzed by AgNO3

S Chiba et al.

CHEMISTRY LETTERS (2006)