4.8 Article

Chiral Phosphoric Acid-Catalyzed Enantioselective Dearomative Electrophilic Hydrazination: Access to Chiral Aza-Quaternary Carbon Indolenines

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

Hypoiodite-Catalyzed Oxidative Umpolung of Indoles forEnantioselective Dearomatization

Hiroki Tanaka et al.

Summary: In this study, we reported the oxidative umpolung of 2,3-disubstituted indoles towards enantioselective dearomative aza-spirocyclization using chiral quaternary ammonium hypoiodite catalysis. Mechanistic studies revealed the reactivity of C3 of indoles by iodination of the indole nitrogen atom. Furthermore, the introduction of pyrazole as an electron-withdrawing auxiliary group at C2 suppressed a competitive dissociative racemic pathway, enabling enantioselective spirocyclization to proceed and providing access to both spiropyrrolidines and four-membered spiroazetidines that are otherwise difficult to obtain.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Co-Catalyzed Direct Regio- and Enantioselective Intermolecular γ-Amination of N-Acylpyrazoles

Xin Fu et al.

Summary: The cobalt-catalyzed regio- and enantioselective gamma-amination of beta,gamma-unsaturated N-acylpyrazoles has been achieved, delivering the corresponding products with good regio- and enantioselectivity. DFT calculations were used to explain the selectivity of this gamma-amination, and the chiral products were easily converted into chiral gamma-amino acid derivatives.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Organocatalytic Direct Asymmetric Indolization from Anilines by Enantioselective [3+2] Annulation

Guan-Jun Wang et al.

Summary: This study describes an efficient method for the synthesis of chiral tetrahydroindole pyrazolinones through chiral phosphoric acid-catalyzed [3 + 2] cascade cyclizations, which exhibit a broad substrate scope, high yields, and excellent enantioselectivities. The research highlights the potential value of direct chiral indolizations from simple amine sources in organic synthesis.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Studies toward the Synthesis of Chartelline C

Yoshiki Nakane et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions

Zi-Lei Xia et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Asymmetric Total Syntheses of the Akuammiline Alkaloids (-)-Strictamine and (-)-Rhazinoline

Wenfei Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)-H Bonds

Dengke Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis

Yuan-Zheng Cheng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids

Weigang He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Total Synthesis of Isodihydrokoumine, (19Z)-Taberpsychine, and (4R)-Isodihydroukoumine N-4-Oxide

Jeff K. Kerkovius et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy

Ye Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Catalytic asymmetric chemodivergent arylative dearomatization of tryptophols

Chun Ma et al.

CHEMICAL COMMUNICATIONS (2017)

Article Multidisciplinary Sciences

Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction

Ji-Wei Zhang et al.

NATURE COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Intermolecular Asymmetric Propargylic Dearomatization of Indoles

Wen Shao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Asymmetric Dearomatization of β-Naphthols through an Amination Reaction Catalyzed by a Chiral Phosphoric Acid

Shou-Guo Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Organocatalytic Asymmetric Arylative Dearomatization of 2,3-Disubstituted Indoles Enabled by Tandem Reactions

Yu-Chen Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Organic

Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (-)-Trigonoliimines

Sunkyu Han et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons

Charles S. Yeung et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (-)-Debromoflustramine B

Zuhui Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Catalytic Asymmetric Dearomatization Reactions

Chun-Xiang Zhuo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Chiral Bronsted acids in enantioselective carbonyl activations - activation modes and applications

Magnus Rueping et al.

CHEMICAL SOCIETY REVIEWS (2011)

Review Chemistry, Organic

Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations

Masahiro Terada

SYNTHESIS-STUTTGART (2010)

Review Chemistry, Multidisciplinary

Stronger bronsted acids

Takahiko Akiyama

CHEMICAL REVIEWS (2007)

Article Chemistry, Organic

The first method for protection-deprotection of the indole 2,3-π bond

PS Baran et al.

ORGANIC LETTERS (2003)