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C-H Activation for Asymmetric Synthesis

C-H Activation for Asymmetric Synthesis

Wydawnictwo VCH
Data wydania 01/09/2019
Wydanie Pierwsze
Liczba stron 296
Forma publikacji książka w twardej oprawie
Poziom zaawansowania Dla profesjonalistów, specjalistów i badaczy naukowych
Język angielski
ISBN 9783527343409
Kategorie Chemia organiczna
592.00 PLN (z VAT)
$157.62 / €134.17 / £120.75 /
Produkt dostępny
Dostawa 2 dni
Do schowka

Opis książki

Provides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry.

C-H Activation for Asymmetric Synthesis

Spis treści

Foreword xi

Part I Asymmetric Activation of C(sp3)-H Bonds 1

Part I.A C(sp3)-H Bond Insertion by Metal Carbenoids and Nitrenoids 2

1 Stereoselective C-C Bond-Forming Reactions Through C(sp3)-H Bond Insertion of Metal Carbenoids 3
Aoife M. Buckley, Thomas A. Brouder, Alan Ford, and Anita R. Maguire

1.1 Introduction 3

1.2 Diazo Compounds 4

1.3 Mechanistic Understanding 5

1.4 Catalysts 7

1.4.1 Copper 7 Bisoxazoline and Schiff Base 7

1.4.2 Rhodium 8 Rhodium(II) Carboxylates 9 Rhodium(II) Carboxamidates 10 Ortho-metalated Complexes 11

1.4.3 Iridium and Ruthenium 11

1.5 Intramolecular C(sp3)-H Bond Insertion 11

1.5.1 Chemoselectivity 13 Catalyst Effects 13 Substrate Effects 14

1.5.2 Regioselectivity 16 Formation of Three-Membered Rings 17 Formation of Four-Membered Rings 18 Formation of Five-Membered Rings 20 Formation of Six-Membered Rings 20

1.5.3 Diastereoselectivity 23 Substrate Effects 23 Catalyst Effects 25

1.5.4 Enantioselectivity 25

1.6 Intermolecular C(sp3)-H Bond Insertion 30

1.6.1 Chemoselectivity 30 Diazo Compounds 32 Catalyst Effects 34 Substrate Functional Groups 35

1.6.2 Regioselectivity 36 Substrate Effects 36 Catalyst Effects 38 Diazo Compound Effects 39

1.6.3 Diastereoselectivity 39 Substrate Effects 39 Catalyst Effects 42

1.6.4 Enantioselectivity 43

1.7 Conclusion 45

References 45

2 Stereoselective C-N Bond-Forming Reactions Through C(sp3)-H Bond Insertion of Metal Nitrenoids 51
Philippe Dauban, Romain Rey-Rodriguez, and Ali Nasrallah

2.1 Introduction 51

2.2 Historical Background 52

2.2.1 Seminal Studies in Catalytic C(sp3)-H Amination 52

2.2.2 Mechanistic and Stereochemical Issues 56

2.3 Catalytic Stereoselective C(sp3)-H Amination Reactions with Iminoiodinanes 60

2.3.1 Catalytic Intermolecular Enantioselective Reactions (Chirality Only on the Metal Complex) 60

2.3.2 Catalytic Intramolecular Enantioselective Reactions 63

2.3.3 Catalytic Intermolecular Diastereoselective Reactions (Chirality on the Metal Complex and the Nitrene Precursor) 66

2.4 Catalytic Stereoselective C(sp3)-H Amination Reactions with Azides 67

2.4.1 Transition Metal-Catalyzed C(sp3)-H Amination Reactions 67

2.4.2 Enzymatic C(sp3)-H Amination Reactions 68

2.5 Catalytic Stereoselective C(sp3)-H Amination Reactions with N-(Sulfonyloxy)carbamates 70

2.6 Conclusion 7

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