Author: Scott Bentley
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles. Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors. Chapter 2 explores the use of the N-benzyl-N-([alpha]-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-([alpha]- methylbenzyl)hydrazine and N -benzyl-N -([alpha]-methylbenzyl)hydroxylamine as chiral ammo- nia and water equivalents respectively. Chapter 3 describes the asymmetric and stereoselective preparation of a range of 4,4- disubstituted isoxazolidin-5-ones from the conjugate addition of lithium (S)-N-tert-butyl- dimethylsilyloxy-N -([alpha]-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding [beta]2,2,3-amino acids. Chapter 4 focuses on the development of a protocol to effect the conjugate addition of a chiral aniline equivalent. The scope of the reaction is delineated by varying both the nu- cleophile and the [alpha],[beta]-unsaturated ester. Finally, cyclisation of the [beta]-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (-)-angustureine is presented. Chapter 5 contains full experimental procedures and characterisation data for all com- pounds synthesised in Chapters 2, 3 and 4.
Asymmetric Conjugate Addition Reactions
Author: Scott Bentley
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles. Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors. Chapter 2 explores the use of the N-benzyl-N-([alpha]-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-([alpha]- methylbenzyl)hydrazine and N -benzyl-N -([alpha]-methylbenzyl)hydroxylamine as chiral ammo- nia and water equivalents respectively. Chapter 3 describes the asymmetric and stereoselective preparation of a range of 4,4- disubstituted isoxazolidin-5-ones from the conjugate addition of lithium (S)-N-tert-butyl- dimethylsilyloxy-N -([alpha]-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding [beta]2,2,3-amino acids. Chapter 4 focuses on the development of a protocol to effect the conjugate addition of a chiral aniline equivalent. The scope of the reaction is delineated by varying both the nu- cleophile and the [alpha],[beta]-unsaturated ester. Finally, cyclisation of the [beta]-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (-)-angustureine is presented. Chapter 5 contains full experimental procedures and characterisation data for all com- pounds synthesised in Chapters 2, 3 and 4.
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
This thesis is concerned with the asymmetric conjugate addition reactions of a range of chiral nucloeophiles. Chapter 1 introduces the conjugate addition reaction as a valuable carbon-carbon and carbon-heteroatom bond forming reaction in organic chemistry, and explores the asymmet- ric conjugate addition of a range of chiral and achiral carbon and nitrogen nucleophiles to a range of acceptors. Chapter 2 explores the use of the N-benzyl-N-([alpha]-methylbenzyl)amino group as a chi- ral auxiliary, by employing the attempted conjugate additions of both N-benzyl-N-([alpha]- methylbenzyl)hydrazine and N -benzyl-N -([alpha]-methylbenzyl)hydroxylamine as chiral ammo- nia and water equivalents respectively. Chapter 3 describes the asymmetric and stereoselective preparation of a range of 4,4- disubstituted isoxazolidin-5-ones from the conjugate addition of lithium (S)-N-tert-butyl- dimethylsilyloxy-N -([alpha]-methylbenzyl)amide. The isoxazolidin-5-ones are then globally de- protected via hydrogenolysis, giving rise to the corresponding [beta]2,2,3-amino acids. Chapter 4 focuses on the development of a protocol to effect the conjugate addition of a chiral aniline equivalent. The scope of the reaction is delineated by varying both the nu- cleophile and the [alpha],[beta]-unsaturated ester. Finally, cyclisation of the [beta]-N-arylamino esters to the corresponding tetrahydroquinolines is explored, and an application to the synthesis of the natural product (-)-angustureine is presented. Chapter 5 contains full experimental procedures and characterisation data for all com- pounds synthesised in Chapters 2, 3 and 4.
Asymmetric Conjugate Addition Reactions
Author: Scott A. Bentley
Publisher:
ISBN:
Category : Asymmetric synthesis
Languages : en
Pages : 0
Book Description
Publisher:
ISBN:
Category : Asymmetric synthesis
Languages : en
Pages : 0
Book Description
Asymmetric Conjugate Addition Reactions
Author: Timothy J. Silcocks
Publisher:
ISBN:
Category : Addition reactions
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category : Addition reactions
Languages : en
Pages :
Book Description
Nickel Catalysis of Asymmetric Conjugate Addition Reactions
Author: Sudipinder K. Sian
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Organocatalytic Enantioselective Conjugate Addition Reactions
Author: Jose L Vicario
Publisher: Royal Society of Chemistry
ISBN: 1849732183
Category : Science
Languages : en
Pages : 365
Book Description
This book, unique in its field, is a comprehensive description of all the methodologies reported for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts (organocatalysts). In the last 3-4 years, this has been a rapidly growing field in organic chemistry, and many papers have appeared reporting excellent protocols for carrying out these highly efficient transformations that compete well with other classical approaches using transition metal catalysts. A particularly attractive feature of this transformation relies upon the fact that the conjugate addition (Michael and Hetero-Michael reactions) is an extraordinarily effective means to initiate cascade processes which result in the formation of complex molecules from very small and simple starting blocks. The book, written by noted experts, covers all recent advances in this hot topic, and provides a good state-of-the-art review for organic chemists working in this field and all those who wish to start projects in this area.
Publisher: Royal Society of Chemistry
ISBN: 1849732183
Category : Science
Languages : en
Pages : 365
Book Description
This book, unique in its field, is a comprehensive description of all the methodologies reported for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts (organocatalysts). In the last 3-4 years, this has been a rapidly growing field in organic chemistry, and many papers have appeared reporting excellent protocols for carrying out these highly efficient transformations that compete well with other classical approaches using transition metal catalysts. A particularly attractive feature of this transformation relies upon the fact that the conjugate addition (Michael and Hetero-Michael reactions) is an extraordinarily effective means to initiate cascade processes which result in the formation of complex molecules from very small and simple starting blocks. The book, written by noted experts, covers all recent advances in this hot topic, and provides a good state-of-the-art review for organic chemists working in this field and all those who wish to start projects in this area.
Nickel Catalysis of Asymmetric Conjugate Addition Reactions
Author: Sudipinder K. Sian
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
Book Description
Catalytic Asymmetric Conjugate Reactions
Author: Armando Cordova
Publisher: John Wiley & Sons
ISBN: 3527632093
Category : Science
Languages : en
Pages : 489
Book Description
This unique and long-awaited handbook on this important topic in the hot field of stereoselective organic synthesis covers several types of nucleophiles. Top international authors deal with modern forms of achieving stereoselective conjugate additions based on the use of chiral auxiliaries or asymmetric catalysis, such as P-N ligands, organocatalysis, domino reactions, Lewis acid and base catalysis. There is also a discussion of the employment of enantioselective conjugate addition transformations in total synthesis of important molecules. With its reliable and previously unpublished experimental procedures, this is a true source of high quality information.
Publisher: John Wiley & Sons
ISBN: 3527632093
Category : Science
Languages : en
Pages : 489
Book Description
This unique and long-awaited handbook on this important topic in the hot field of stereoselective organic synthesis covers several types of nucleophiles. Top international authors deal with modern forms of achieving stereoselective conjugate additions based on the use of chiral auxiliaries or asymmetric catalysis, such as P-N ligands, organocatalysis, domino reactions, Lewis acid and base catalysis. There is also a discussion of the employment of enantioselective conjugate addition transformations in total synthesis of important molecules. With its reliable and previously unpublished experimental procedures, this is a true source of high quality information.
Catalysis in Asymmetric Synthesis
Author: Vittorio Caprio
Publisher: John Wiley & Sons
ISBN: 1405190914
Category : Science
Languages : en
Pages : 409
Book Description
Asymmetric synthesis has become a major aspect of modern organic chemistry. The stereochemical properties of an organic compound are often essential to its bioactivity, and the need for stereochemically pure pharmaceutical products is a key example of the importance of stereochemical control in organic synthesis. However, achieving high levels of stereoselectivity in the synthesis of complex natural products represents a considerable intellectual and practical challenge for chemists. Written from a synthetic organic chemistry perspective, this text provides a practical overview of the field, illustrating a wide range of transformations that can be achieved. The book captures the latest advances in asymmetric catalysis with emphasis placed on non-enzymatic methods. Topics covered include: Reduction of alkenes, ketones and imines Nucleophilic addition to carbonyl compounds Catalytic carbon-carbon bond forming reactions Catalytic reactions involving metal carbenoids Conjugate addition reactions Catalysis in Asymmetric Synthesis bridges the gap between undergraduate and advanced level textbooks and provides a convenient point of entry to the primary literature for the experienced synthetic organic chemist.
Publisher: John Wiley & Sons
ISBN: 1405190914
Category : Science
Languages : en
Pages : 409
Book Description
Asymmetric synthesis has become a major aspect of modern organic chemistry. The stereochemical properties of an organic compound are often essential to its bioactivity, and the need for stereochemically pure pharmaceutical products is a key example of the importance of stereochemical control in organic synthesis. However, achieving high levels of stereoselectivity in the synthesis of complex natural products represents a considerable intellectual and practical challenge for chemists. Written from a synthetic organic chemistry perspective, this text provides a practical overview of the field, illustrating a wide range of transformations that can be achieved. The book captures the latest advances in asymmetric catalysis with emphasis placed on non-enzymatic methods. Topics covered include: Reduction of alkenes, ketones and imines Nucleophilic addition to carbonyl compounds Catalytic carbon-carbon bond forming reactions Catalytic reactions involving metal carbenoids Conjugate addition reactions Catalysis in Asymmetric Synthesis bridges the gap between undergraduate and advanced level textbooks and provides a convenient point of entry to the primary literature for the experienced synthetic organic chemist.
Metal-catalyzed Asymmetric Conjugate Addition Reaction of Aryl Alanes to Cyclic Enones
Author: Christine Hawner
Publisher:
ISBN:
Category :
Languages : en
Pages : 145
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 145
Book Description
Advances in Asymmetric Synthesis
Author: Bozzano G Luisa
Publisher: Elsevier
ISBN: 0080552005
Category : Science
Languages : en
Pages : 329
Book Description
Advances in Asymmetric Synthesis
Publisher: Elsevier
ISBN: 0080552005
Category : Science
Languages : en
Pages : 329
Book Description
Advances in Asymmetric Synthesis