Knowledge Updates 2016/2 / by: Marek, I., Murai, T., Stoltz, B. M..

Format:

Book

Author/Creator:

Bruffaerts, J., Author.

Chciuk, T., Author.

Flowers, R., Author.

Fujioka, H., Author.

Ishii, A., Author.

Jiang, X., Author.

Kimura, T., Author.

Li, Y., Author.

Murai, K., Author.

Nokami, T., Author.

Tsubouchi, A., Author.

Vasseur, A., Author.

Xie, W., Author.

Yoshimatsu, M., Author.

Contributor:

Marek, I., Editor.

Murai, T., Editor.

Stoltz, B. M., Editor.

Series:

Science of Synthesis.

Science of Synthesis. 2510-5469

Language:

English

Subjects (All):

Chemistry, Organic.

Physical Description:

1 online resource (520 pages) : illustrations

Vol. 1 (2001)-

Edition:

1st ed.

Place of Publication:

Stuttgart, [Germany] ; New York : Georg Thieme Verlag KG, 2016.

Summary:

The Science of Synthesis Editorial Board, together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Several annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.

Contents:

Science of Synthesis: Knowledge Updates 2016/2

Title Page

Copyright

Preface

Abstracts

Science of Synthesis Knowledge Updates 2016/2

Table of Contents

1.2.7 Radical-Based Palladium-Catalyzed Bond Constructions

1.2.7.1 Method 1: Reactions Involving Palladium(I) Species

1.2.7.1.1 Variation 1: Synthesis of Organometallic Palladium(I) Complexes

1.2.7.1.2 Variation 2: Reactions Involving Palladium(I) Precatalysts

1.2.7.1.3 Variation 3: Cross-Coupling Reactions

1.2.7.1.4 Variation 4: Carbonylation Reactions

1.2.7.1.5 Variation 5: Cyclization Reactions

1.2.7.1.6 Variation 6: Atom-Transfer Reactions

1.2.7.2 Method 2: Reactions Involving Palladium(III) Species

1.2.7.2.1 Variation 1: Synthesis of Organometallic Palladium(III) Complexes

1.2.7.2.2 Variation 2: C-H Activation Reactions Involving Palladium(III)

1.2.7.2.3 Variation 3: C-F Bond-Constructing Reactions Involving Palladium(III)

1.2.7.2.4 Variation 4: Reactions Involving Phenyl or Benzoyl Radicals

1.2.7.2.5 Variation 5: Asymmetric Aza-Claisen Rearrangements

1.2.7.3 Method 3: Reactions Involving Palladium(I) and Palladium(III) Species

1.2.7.4 Method 4: Miscellaneous Reactions

2.11.15 C(sp3)-H Functionalization by Allylic C-H Activation of Zirconocene Complexes

2.11.15.1 Method 1: Synthesis of Conjugated Dienes from Nonconjugated Dienes

2.11.15.1.1 Variation 1: From Nonheteroatom-Substituted Alkenes

2.11.15.1.2 Variation 2: From Nonconjugated Dienes Bearing an Alkoxy Substituent

2.11.15.2 Method 2: Synthesis of Trienes

2.11.15.3 Method 3: Synthesis of Homoallylic Alcohols

2.11.15.3.1 Variation 1: From Acid Chlorides without Ligand Exchange

2.11.15.3.2 Variation 2: From Acid Chlorides with Ligand Exchange

2.11.15.3.3 Variation 3: From Aldehydes without Ligand Exchange.

2.11.15.3.4 Variation 4: From Aldehydes with Ligand Exchange

2.11.15.4 Method 4: Diastereoselective Synthesis of Homoallylic Amines

2.11.15.5 Method 5: Diastereoselective Synthesis of 1,4-Homoallylic Diols

2.11.15.5.1 Variation 1: From Grignard Reagents

2.11.15.5.2 Variation 2: From Terminal Alkenes

2.11.15.6 Method 6: Synthesis of 1,2-Disubstituted Cyclopropanols

2.11.15.7 Method 7: Synthesis of Substituted Allylic Derivatives from Unsaturated Fatty Alcohols

2.11.15.8 Method 8: Selective Reduction of the Double Bond of ω-Ene Dihydrofurans and Dihydropyrans

2.11.15.9 Method 9: Synthesis of Acyclic Fragments Possessing an All-Carbon Quaternary Stereogenic Center

2.11.15.9.1 Variation 1: From ω-Ene Cyclopropanes

2.11.15.9.2 Variation 2: From Alkylidenecyclopropanes

2.11.15.9.3 Variation 3: From ω-Alkenylcyclopropanes Bearing a Leaving Group

2.11.16 Synthesis and Reactivity of Heteroatom-Substituted Vinylzirconocene Derivatives and Hetarylzirconocenes

2.11.16.1 General Preparation of Vinylzirconocene Derivatives

2.11.16.2 General Reactivity of Vinylzirconocene Derivatives

2.11.16.3 Preparation of Vinylzirconocene Derivatives from Heteroatom-Substituted Alkenes

2.11.16.3.1 Method 1: From Alkenyl Halides

2.11.16.3.2 Method 2: From Aryl Halides

2.11.16.3.3 Method 3: From Enol Sulfonates

2.11.16.3.4 Method 4: From Enol Ethers and Silyl Enol Ethers

2.11.16.3.5 Method 5: From Sulfides, Sulfoxides, and Sulfones

2.11.16.3.6 Method 6: From Carbamates

2.11.16.3.7 Method 7: From Dienyl Systems

2.12.17 The Role of Solvents and Additives in Reactions of Samarium(II) Iodide and Related Reductants

2.12.17.1 Synthesis of Samarium(II) Reductants

2.12.17.1.1 Samarium(II) Iodide

2.12.17.1.1.1 Method 1: Synthesis in Tetrahydrofuran from Samarium and 1,2-Diiodoethane.

2.12.17.1.1.2 Method 2: Synthesis in Tetrahydrofuran from Samarium and Iodine

2.12.17.1.1.3 Method 3: Synthesis in Tetrahydropyran

2.12.17.1.1.4 Method 4: Synthesis in 1,2-Dimethoxyethane

2.12.17.1.1.5 Method 5: Synthesis in Acetonitrile and Other Nitriles

2.12.17.1.1.6 Method 6: Synthesis in Benzene/Hexamethylphosphoric Triamide

2.12.17.1.2 Samarium(II) Bromide and Samarium(II) Chloride

2.12.17.1.2.1 Method 1: Synthesis of Samarium(II) Bromide from Samarium(III) Oxide and Hydrobromic Acid

2.12.17.1.2.2 Method 2: Synthesis of Samarium(II) Bromide from Samarium and 1,1,2,2-Tetrabromoethane

2.12.17.1.2.3 Method 3: Synthesis of Samarium(II) Bromide from Samarium(II) Iodide and Lithium Bromide

2.12.17.1.2.4 Method 4: Synthesis of Samarium(II) Chloride from Samarium(III) Chloride

2.12.17.1.2.5 Method 5: Synthesis of Samarium(II) Chloride from Samarium(II) Iodide and Lithium Chloride

2.12.17.1.2.6 Method 6: Synthesis of Samarium(II) Chloride in Water from Samarium(III) Chloride and Samarium

2.12.17.1.3 Samarium(II) Trifluoromethanesulfonate

2.12.17.1.3.1 Method 1: Synthesis from Samarium(III) Trifluoromethanesulfonate, Samarium Metal, and Ethylmagnesium Bromide

2.12.17.1.3.2 Method 2: Synthesis from Samarium(III) Trifluoromethanesulfonate and sec-Butyllithium

2.12.17.1.3.3 Method 3: Synthesis from Samarium Metal and 1,5-Dithioniabicyclo[ 3.3.0]octane Bis(trifluoromethanesulfonate)

2.12.17.1.3.4 Method 4: Mercury-Catalyzed Reduction of Samarium(III) Trifluoromethanesulfonate

2.12.17.1.3.5 Method 5: Synthesis from Samarium(III) Trifluoromethanesulfonate and Samarium Metal

2.12.17.1.4 Samarium(II) Amides

2.12.17.1.5 (η5-Cyclopentadienyl)samarium(II) Complexes

2.12.17.1.5.1 Method 1: Synthesis of Bis(η5-cyclopentadienyl)samarium(II).

2.12.17.1.5.2 Method 2: Synthesis of Bis(η5-pentamethylcyclopentadienyl) samarium(II)

2.12.17.2 Use of Lewis Bases in Samarium(II)-Based Reactions

2.12.17.2.1 Hexamethylphosphoric Triamide

2.12.17.2.1.1 Method 1: Reduction of Alkyl and Aryl Halides

2.12.17.2.1.2 Method 2: Reduction of α-Oxygenated Carbonyl Compounds

2.12.17.2.1.3 Method 3: Reduction of 4-Methylbenzoates

2.12.17.2.1.4 Method 4: Grignard and Barbier Reactions

2.12.17.2.1.4.1 Variation 1: Intermolecular Samarium Grignard Reactions

2.12.17.2.1.4.2 Variation 2: Intermolecular Samarium Barbier Reactions

2.12.17.2.1.4.3 Variation 3: Intramolecular Samarium Barbier Reactions

2.12.17.2.1.5 Method 5: Reformatsky- and Aldol-Type Reactions

2.12.17.2.1.6 Method 6: Halide-Alkene Coupling Reactions

2.12.17.2.1.7 Method 7: Spirocyclization via Intramolecular Aryl Iodide Radical Addition

2.12.17.2.1.8 Method 8: Carbonyl-Alkene Coupling

2.12.17.2.1.8.1 Variation 1: Intramolecular Cyclization of Unactivated Alkenyl Ketones

2.12.17.2.1.8.2 Variation 2: Sequential Intramolecular Cyclization with Intermolecular Electrophilic Addition

2.12.17.2.1.8.3 Variation 3: Intermolecular Ketone-Allene Coupling

2.12.17.2.1.8.4 Variation 4: Sequential Intramolecular Cyclization with Electrophilic Addition to 1H-Indole Derivatives

2.12.17.2.1.9 Method 9: Intramolecular Pinacol Coupling of Carbonyl Compounds

2.12.17.2.1.10 Method 10: Intramolecular Pinacol-Type Coupling of Ketones and Imines

2.12.17.2.1.11 Method 11: Tandem Epoxide-Opening/Cyclization To Afford γ-Lactones

2.12.17.2.1.12 Method 12: Tandem Elimination and Coupling of Aliphatic Imides with Carbonyl Compounds

2.12.17.2.1.13 Method 13: Intermolecular and Intramolecular Reductive Dimerization

2.12.17.2.2 Additives Related to Hexamethylphosphoric Triamide.

2.12.17.2.2.1 Method 1: Tri(pyrrolidin-1-yl)phosphine Oxide in Reductive Coupling Reactions

2.12.17.2.2.2 Method 2: N-Methyl-P,P-di(pyrrolidin-1-yl)phosphinic Amide in Reductive Cyclization Reactions

2.12.17.2.2.3 Method 3: Hydroxylated Hexamethylphosphoric Triamide in Reductive Coupling Reactions

2.12.17.3 Use of Proton Donors in Samarium(II)-Based Reactions

2.12.17.3.1 Water

2.12.17.3.1.1 Method 1: Reduction of Alkyl Iodides

2.12.17.3.1.2 Method 2: Reduction of Aromatic Carboxylic Acids, Esters, Amides, and Nitriles

2.12.17.3.1.3 Method 3: Reduction of Azido Oligosaccharides to Amino Sugars

2.12.17.3.1.4 Method 4: Reduction of Six-Membered Lactones

2.12.17.3.1.5 Method 5: Reduction of Cyclic Esters

2.12.17.3.1.6 Method 6: Reductive Cyclization of Lactones

2.12.17.3.1.7 Method 7: Reduction of Sodium S-Alkyl Thiosulfates and Alkyl Thiocyanates

2.12.17.3.1.8 Method 8: Reduction of Cyclic 1,3-Diesters

2.12.17.3.1.9 Method 9: Cross Coupling of N-Acyloxazolidinones to Acrylamides and Acrylates

2.12.17.3.1.10 Method 10: Coupling To Produce α,α-Disubstituted Pyrrolidin-2-ylmethanols

2.12.17.3.1.11 Method 11: Reductive Coupling of Nitrones and Acrylates

2.12.17.3.2 Water and Amines

2.12.17.3.2.1 Method 1: Reduction of Ketones

2.12.17.3.2.2 Method 2: Reduction of β-Hydroxy Ketones

2.12.17.3.2.3 Method 3: Reduction of Alkyl Halides

2.12.17.3.2.4 Method 4: Reduction of Double and Triple Bonds in Conjugated Alkenes

2.12.17.3.2.5 Method 5: Deprotection of Allyl Ether Protected Alcohols

2.12.17.3.2.6 Method 6: Deprotection of Toluenesulfonamides

2.12.17.3.2.7 Method 7: Reduction of Nitroalkanes

2.12.17.3.2.8 Method 8: Reductive Cleavage of Benzyl-Heteroatom Bonds

2.12.17.3.2.9 Method 9: Reduction of Nitriles

2.12.17.3.2.10 Method 10: Reduction of Unactivated Esters.

2.12.17.3.2.11 Method 11: Reduction of Amides to Alcohols.

Notes:

Includes bibliographical references at the end of each chapters and index.

Print version record.

ISBN:

9783132403680

3132403687

9783132209015

3132209015

OCLC:

969637135