☆ 4.8 Article

Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines

ORGANIC LETTERS (2022)

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

Chiral Selenide/Achiral Sulfonic Acid Cocatalyzed Atroposelective Sulfenylation of Biaryl Phenols via a Desymmetrization/Kinetic Resolution Sequence

Hui-Yun Luo et al.

Summary: The enantioselective synthesis of axially chiral sulfur-containing biaryl derivatives through electrophilic sulfenylation of biaryl phenols has been achieved for the first time. The reaction is facilitated by a novel 3,3'-disubstituted BINOL-derived selenide catalyst and an achiral sulfonic acid. Control experiments and computational studies demonstrate that multiple noncovalent interactions, particularly a network of hydrogen bond interactions, play a crucial role in determining enantioselectivity and reactivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Sulfide/Phosphoric Acid Cocatalyzed Enantioselective Intermolecular Oxysulfenylation of Alkenes with Phenol and Alcohol O-Nucleophiles

Xiao-Dong Liu et al.

Summary: Enantioselective intermolecular three-component oxysulfenylations of alkenes with phenols and alcohols as O-nucleophiles were achieved using chiral BINAM-derived sulfide/phosphoric acid as the co-catalyst. This protocol exhibited a broad substrate scope and excellent selectivity.

CCS CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic enantioselective oxysulfenylation of o-vinylanilides

Arunachalam Kesavan et al.

Summary: This paper demonstrates the successful enantioselective oxysulfenylation of o-vinylanilides with N-(aryl/alkylthio)imides using Tf2NH-assisted BINAM-derived thiophosphoramide catalysis. The reaction yields diverse substituted aryl/alkylthio tethered 3,1-benzoxazines with excellent enantiomeric ratios. Additionally, the synthetic applications of benzoxazines and aryl/alkylthio moieties, as well as a transition state model for the observed enantioselectivity, are discussed.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Cobalt(II) Complex Catalyzed Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Selenides with α-Diazo Pyrazoleamides

Xiaobin Lin et al.

Summary: This study presents a novel asymmetric [2,3]-sigmatropic rearrangement catalyzed by a chiral N,N'-dioxide/cobalt(II) complex, resulting in the efficient synthesis of optically active selenides with high yields and enantiomeric excess. Control experiments demonstrated the reactivity of allylic selenides and the advantages of the catalyst and a-diazo pyrazoleamide in the rearrangement process.

CCS CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes

Quanbin Jiang et al.

Summary: Chiral organosulfur compounds have wide applications in medicinal chemistry and asymmetric synthesis. The development of methods for their preparation is crucial in organic synthetic chemistry. Enantioselective electrophilic thiolation of alkenes is a straightforward pathway for synthesizing chiral sulfides, and our group has successfully designed and applied chiral bifunctional chalcogenide catalysts for this purpose.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes

Yaoyu Liang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines

Subramani Rajkumar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Organic

Enantioselective Syntheses of 4H-3,1-Benzoxazines via Catalytic Asymmetric Chlorocyclization of o-Vinylanilides

Qinxia Xie et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

Anastassia Matviitsuk et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Lewis Base/Bronsted Acid Co-catalyzed Enantioselective Sulfenylation/Semipinacol Rearrangement of Di- and Trisubstituted Allylic Alcohols

Yu-Yang Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes

Aaron Roth et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Review Chemistry, Organic

Recent progress in selenium-catalyzed organic reactions

Lixiong Shao et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Selenide-Catalyzed Enantioselective Allylic Reaction and Intermolecular Difunctionalization of Alkenes: Efficient Construction of C-SCF3 Stereogenic Molecules

Xiang Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

Zhonglin Tao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Physical

Desymmetrizing Enantio- and Diastereoselective Selenoetherification through Supramolecular Catalysis

Jie Yang See et al.

ACS CATALYSIS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

Xiang Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Organic

Catalytic and Highly Enantioselective Selenolactonization

Wenxue Niu et al.

ORGANIC LETTERS (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Selenocyclization via Dynamic Kinetic Resolution of Seleniranium Ions by Hydrogen-Bond Donor Catalysts

Hu Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes

Scott E. Denmark et al.

NATURE CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

Depeng Zhao et al.

CHEMICAL SCIENCE (2014)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

Qiang Wei et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Halocyclization Using Reagents Tailored for Chiral Anion Phase-Transfer Catalysis

Yi-Ming Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Article Chemistry, Organic

Enantioselective oxysulfenylation and oxyselenenylation of olefins catalyzed by chiral Bronsted acids

Huan Guan et al.

TETRAHEDRON (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes

Scott E. Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Preparative and Mechanistic Studies toward the Rational Development of Catalytic, Enantioselective Selenoetherification Reactions

Scott E. Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Observation of Direct Sulfenium and Selenenium Group Transfer from Thiiranium and Seleniranium Ions to Alkenes

Scott E. Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Review Chemistry, Multidisciplinary

Lewis base catalysis in organic synthesis

Scott E. Denmark et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic highly enantioselective α-selenenylation of aldehydes

Henrik Sunden et al.

TETRAHEDRON LETTERS (2007)

添加到收藏夹

Article Chemistry, Organic

Lewis base activation of lewis acids: Development of a Lewis base catalyzed selenolactonization

Scott E. Denmark et al.

ORGANIC LETTERS (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Organocatalytic asymmetiric alpha-selenenylation of aldehydes

Marcello Tiecco et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

添加到收藏夹

Article Chemistry, Organic

On the mechanism of the selenolactonization reaction with selenenyl halides

Scott E. Denmark et al.

JOURNAL OF ORGANIC CHEMISTRY (2006)

添加到收藏夹

Article Chemistry, Organic

Optically active seleninamides: Isolation, absolute configuration, and racemization mechanism

Y Nakashima et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

添加到收藏夹

Review Chemistry, Multidisciplinary

Organoselenium and organotellurium compounds: Toxicology and pharmacology

CW Nogueira et al.

CHEMICAL REVIEWS (2004)

添加到收藏夹

Article Chemistry, Medicinal

6-aryl-1,4-dihydro-benzo[d][1,3]oxazin-2-ones:: A novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists

PW Zhang et al.

JOURNAL OF MEDICINAL CHEMISTRY (2002)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chemistry of biologically important synthetic organoselenium compounds

G Mugesh et al.

CHEMICAL REVIEWS (2001)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.