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A trinuclear Cu2Eu complex catalyzed asymmetric Friedel–Crafts alkylations of indoles with nitroalkenes

Guoqi Zhang, G. Zhang

Inorganic Chemistry Communications > 2014 > 40 > Complete > 1-4

Catalytic enantioselective Friedel–Crafts alkylations of indoles and nitroalkenes were carried out by using a new heterotrimetallic Cu/Eu/Cu complex catalyst based on the simple chiral ligand, reduced Schiff base 1, to give the Friedel–Crafts adducts with up to 88% yield and 80% ee. The trimetallic catalyst is air-stable and can be formed in-situ by a facile solution self-assembly during the catalytic...

article

Recent developments in enantioselective multicatalysed tandem reactions

Hélène Pellissier, H. Pellissier

Tetrahedron > 2013 > 69 > 35 > 7171-7210

This review is intended to cover the recent developments in the asymmetric tandem reactions induced by multiple catalysts including metals, organocatalysts, as well as enzymes, focussing on those published since the beginning of 2010. In the last three years, multicatalystpromoted asymmetric tandem reactions have emerged as a novel powerful strategy to maximise synthetic efficiency, allowing an increasing...

chapter

Michael Addition

Jesús M. García, Mikel Oiarbide, Claudio Palomo, Giuseppe Bartoli, more

Catalytic Asymmetric Friedel–Crafts Alkylations > 17 - 99

This chapter contains sections titled: Chelating α,β‐Unsaturated Compounds Abbreviations Simple α,β‐Unsaturated Substrates Nitroalkenes Acknowledgments Summary References

article

Switchable Chemo‐, Regio‐ and Pseudo‐Stereodivergence in Palladium‐Catalyzed Cycloaddition of Allenes

Pengfei Luo, Jinxia Li, Yu‐Hua Deng, Peiyuan Yu, more

Angewandte Chemie International Edition > 63 > 45 > n/a - n/a

Here, we report a strategy enabling triple switchable chemo‐, regio‐, and stereodivergence in newly developed palladium‐catalyzed cycloadditions of allenes. An asymmetric pseudo‐stereodivergent cycloaddition of allenes bearing a primary leaving group at the α‐position, where a dynamic kinetic asymmetric hydroalkoxylation of racemic unactivated allenes was the enantio‐determining step, is realized,...

article

Switchable Chemo‐, Regio‐ and Pseudo‐Stereodivergence in Palladium‐Catalyzed Cycloaddition of Allenes

Pengfei Luo, Jinxia Li, Yu‐Hua Deng, Peiyuan Yu, more

Angewandte Chemie > 136 > 45 > n/a - n/a

Here, we report a strategy enabling triple switchable chemo‐, regio‐, and stereodivergence in newly developed palladium‐catalyzed cycloadditions of allenes. An asymmetric pseudo‐stereodivergent cycloaddition of allenes bearing a primary leaving group at the α‐position, where a dynamic kinetic asymmetric hydroalkoxylation of racemic unactivated allenes was the enantio‐determining step, is realized,...

article

Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations

Shaoze Yu, Mengyao Yuan, Wansen Xie, Zidan Ye, more

Angewandte Chemie International Edition > 63 > 45 > n/a - n/a

Inherently chiral calix[4]arenes represent a unique type of chiral molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the catalytic enantioselective synthesis of inherently chiral calix[4]arenes through the sequential organocatalyzed enantioselective Povarov reaction and aromatizations. The chiral phosphoric acid...

article

Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations

Shaoze Yu, Mengyao Yuan, Wansen Xie, Zidan Ye, more

Angewandte Chemie > 136 > 45 > n/a - n/a

Inherently chiral calix[4]arenes represent a unique type of chiral molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the catalytic enantioselective synthesis of inherently chiral calix[4]arenes through the sequential organocatalyzed enantioselective Povarov reaction and aromatizations. The chiral phosphoric acid...

article

Palladium‐Catalyzed Enantioselective Migratory Hydroamidocarbonylation of Amide‐Linked Alkenes to Access Chiral α‐Alkyl Succinimides

Zhen Wang, Chaoren Shen, Kaiwu Dong

Angewandte Chemie International Edition > 63 > 43 > n/a - n/a

A Pd‐catalyzed asymmetric isomerization‐hydroamidocarbonylation of amide‐containing alkenes was developed, affording a variety of chiral α‐alkyl succinimides in moderate to good yields with high enantioselectivities. The key to success was introducing bulky 1‐adamentyl P‐substitution and 2,3,5,6‐tetramethoxyphenyl group into the rigid P‐chirogenic bisphosphine ligand to create stronger steric hinderance...

article

Palladium‐Catalyzed Enantioselective Migratory Hydroamidocarbonylation of Amide‐Linked Alkenes to Access Chiral α‐Alkyl Succinimides

Zhen Wang, Chaoren Shen, Kaiwu Dong

Angewandte Chemie > 136 > 43 > n/a - n/a

A Pd‐catalyzed asymmetric isomerization‐hydroamidocarbonylation of amide‐containing alkenes was developed, affording a variety of chiral α‐alkyl succinimides in moderate to good yields with high enantioselectivities. The key to success was introducing bulky 1‐adamentyl P‐substitution and 2,3,5,6‐tetramethoxyphenyl group into the rigid P‐chirogenic bisphosphine ligand to create stronger steric hinderance...

article

Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles

Yu‐Lin Gao, Yang Yang, Chen Wu, Ming‐Sheng Xie, more

Chemistry – A European Journal > 30 > 56 > n/a - n/a

Despite the existence of three competing reactions for propargyloxyoxindoles, we report a chemoselectivity switch between enantioselective propargyl [2,3]‐Wittig rearrangement and Conia‐ene‐type reactions, with suppression of the [1,2]‐Wittig‐type rearrangement. Using C₁‐symmetric imidazolidine‐pyrroloimidazolone pyridine as the ligand and Ni(acac)₂ as the Lewis acid, diverse 3‐hydroxy 3‐substituted...

article

Efficient Synthesis of a C₂‐Symmetric 2,2′‐Bipyridine‐α,α′‐1‐t–butyl‐diol Ligand by Stereoselective Double Hydrogen Transfer to a 2,2′‐Bipyridine‐diketone

Stéphany Bouzid, Antony Marcoux, Thierry Ollevier

Chemistry – A European Journal > 30 > 56 > n/a - n/a

An efficient and practical method was developed for the synthesis of C₂‐symmetric 2,2′‐bipyridine‐α,α′‐1‐t‐butyl‐diol ligands. The disclosed synthesis involves the Ullmann homocoupling of a keto bromo‐pyridine under NiCl₂/Zn/PPh₃ conditions, followed by the stereoselective double hydrogen transfer to the obtained 2,2′‐bipyridine‐diketone using Ru^II Noyori–Ikariya catalysts. This approach allowed the...

article

Recent Advances on Catalytic Atroposelective Synthesis of Planar‐Chiral Macrocycles

Gongming Yang, Jian Wang

Angewandte Chemie > 136 > 42 > n/a - n/a

Planar‐chiral skeletons widely exist in natural products, bioactive compounds, and other functional molecules. Although significant progress has been made in the field of asymmetric synthesis of centrally or axially chiral molecules over the past years, enantioselective constructing of planar chirality is still a big obstacle and numerous efforts have been made in this field. Previous works have mainly...

article

Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols

Ping Wu, Wen‐Tao Zhang, Ji‐Xiang Yang, Xian‐Yang Yu, more

Angewandte Chemie > 136 > 42 > n/a - n/a

Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery of their applications have become significant but challenging issues in the scientific community due to the unique structures of this class of atropisomers. We herein report the first catalytic atroposelective preparation of cyclopentenyl[b]indoles, a new kind of alkene atropisomers, with...

article

Recent Advances on Catalytic Atroposelective Synthesis of Planar‐Chiral Macrocycles

Gongming Yang, Jian Wang

Angewandte Chemie International Edition > 63 > 42 > n/a - n/a

Planar‐chiral skeletons widely exist in natural products, bioactive compounds, and other functional molecules. Although significant progress has been made in the field of asymmetric synthesis of centrally or axially chiral molecules over the past years, enantioselective constructing of planar chirality is still a big obstacle and numerous efforts have been made in this field. Previous works have mainly...

article

Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols

Ping Wu, Wen‐Tao Zhang, Ji‐Xiang Yang, Xian‐Yang Yu, more

Angewandte Chemie International Edition > 63 > 42 > n/a - n/a

Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery of their applications have become significant but challenging issues in the scientific community due to the unique structures of this class of atropisomers. We herein report the first catalytic atroposelective preparation of cyclopentenyl[b]indoles, a new kind of alkene atropisomers, with...

article

Computational Insights into Cinchona‐Based Phase Transfer Catalysis for Asymmetric Conjugate Cyanation

Iñigo Iribarren, Maxime Ferrer, Ibon Alkorta, Cristina Trujillo

European Journal of Organic Chemistry > 27 > 37 > n/a - n/a

The synthesis of asymmetric organic molecules has experienced a huge development over the last few decades. Phase‐transfer catalysis has been proven to be one of the most powerful methods for these asymmetric transformations. However, the study of the mechanism of these catalysts and the different interactions that they can establish with the reactants has failed to keep pace. In the present study,...

article

Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β‐Unsaturated Amides: Efficient Access to Chiral β‐Amino Amides^†

Bing Jiao, Fangyuan Wang, Hui Lv

Chinese Journal of Chemistry > 42 > 21 > 2641 - 2646

The first asymmetric hydrogenation of acyclic tetrasubstituted α,β‐unsaturated amides has been achieved by using Rh/DuanPhos complex as a catalyst, delivering chiral β‐amino amides with two contiguous chiral centers in excellent yields and high enantioselectivities (up to 99% yield, 96% ee), which provides efficient and concise access to valuable β‐amino amide derivatives. The gram‐scale reaction...

article

A Dual Cobalt‐Photoredox Catalytic Approach for Asymmetric Dearomatization of Indoles with Aryl Amides via C−H Activation

Abir Das, Subramani Kumaran, Harihara Subramanian Ravi Sankar, J. Richard Premkumar, more

Angewandte Chemie International Edition > 63 > 40 > n/a - n/a

In this study, we unveil a novel method for the asymmetric dearomatization of indoles under cobalt/photoredox catalysis. By strategically activating C−H bonds of amides and subsequent migratory insertion of π‐bonds present in indole as reactive partner, we achieve syn‐selective tetrahydro‐5H‐indolo[2,3‐c]isoquinolin‐5‐one derivatives with excellent yields and enantiomeric excesses of up to >99...

article

A Dual Cobalt‐Photoredox Catalytic Approach for Asymmetric Dearomatization of Indoles with Aryl Amides via C−H Activation

Abir Das, Subramani Kumaran, Harihara Subramanian Ravi Sankar, J. Richard Premkumar, more

Angewandte Chemie > 136 > 40 > n/a - n/a

In this study, we unveil a novel method for the asymmetric dearomatization of indoles under cobalt/photoredox catalysis. By strategically activating C−H bonds of amides and subsequent migratory insertion of π‐bonds present in indole as reactive partner, we achieve syn‐selective tetrahydro‐5H‐indolo[2,3‐c]isoquinolin‐5‐one derivatives with excellent yields and enantiomeric excesses of up to >99...

article

Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes

Kairi Yamashiro, Kohei Fujii, Yu Sato, Koji Masutomi, more

Angewandte Chemie International Edition > 63 > 38 > n/a - n/a

We have developed the Rh‐catalyzed enantioselective [2+2+2] cycloaddition of homopropargyl enamides (tosylamide‐tethered 1,6‐enynes) with alkynes to construct tetrahydroindole skeletons found in natural alkaloids and pharmaceuticals. This cycloaddition proceeds at room temperature in high yields and regio‐ and enantioselectivity with a broad substrate scope. The preparative scale reaction followed...

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Search results

A trinuclear Cu2Eu complex catalyzed asymmetric Friedel–Crafts alkylations of indoles with nitroalkenes

Recent developments in enantioselective multicatalysed tandem reactions

Michael Addition

Switchable Chemo‐, Regio‐ and Pseudo‐Stereodivergence in Palladium‐Catalyzed Cycloaddition of Allenes

Switchable Chemo‐, Regio‐ and Pseudo‐Stereodivergence in Palladium‐Catalyzed Cycloaddition of Allenes

Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations

Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations

Palladium‐Catalyzed Enantioselective Migratory Hydroamidocarbonylation of Amide‐Linked Alkenes to Access Chiral α‐Alkyl Succinimides

Palladium‐Catalyzed Enantioselective Migratory Hydroamidocarbonylation of Amide‐Linked Alkenes to Access Chiral α‐Alkyl Succinimides

Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles

Efficient Synthesis of a C₂‐Symmetric 2,2′‐Bipyridine‐α,α′‐1‐t–butyl‐diol Ligand by Stereoselective Double Hydrogen Transfer to a 2,2′‐Bipyridine‐diketone

Recent Advances on Catalytic Atroposelective Synthesis of Planar‐Chiral Macrocycles

Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols

Recent Advances on Catalytic Atroposelective Synthesis of Planar‐Chiral Macrocycles

Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols

Computational Insights into Cinchona‐Based Phase Transfer Catalysis for Asymmetric Conjugate Cyanation

Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β‐Unsaturated Amides: Efficient Access to Chiral β‐Amino Amides^†

A Dual Cobalt‐Photoredox Catalytic Approach for Asymmetric Dearomatization of Indoles with Aryl Amides via C−H Activation

A Dual Cobalt‐Photoredox Catalytic Approach for Asymmetric Dearomatization of Indoles with Aryl Amides via C−H Activation

Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes

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