New PDF release: Catalytic Asymmetric Conjugate Reactions

By Armando Cordova

ISBN-10: 3527324119

ISBN-13: 9783527324118

ISBN-10: 3527630570

ISBN-13: 9783527630578

Content material:
Chapter 1 Rhodium? and Palladium?Catalyzed uneven Conjugate Additions (pages 1–70): Guillaume Berthon and Tamio Hayashi
Chapter 2 Cu? and Ni?Catalyzed Conjugated Additions of Organozincs and Organoaluminums to ?,??Unsaturated Carbonyl Compounds (pages 71–144): Martin Kotora and Robert Betik
Chapter three ECAs of Organolithium Reagents, Grignard Reagents, and Examples of Cu?Catalyzed ECAs (pages 145–167): Gui?Ling Zhao and Armando Cordova
Chapter four uneven Bifunctional Catalysis utilizing Heterobimetallic and Multimetallic structures in Enantioselective Conjugate Additions (pages 169–190): Prof. Armando Cordova
Chapter five Enamines in Catalytic Enantioselective Conjugate Additions (pages 191–218): Ramon Rios and Albert Moyano
Chapter 6 Iminium Activation in Catalytic Enantioselective Conjugate Additions (pages 219–293): Jose L. Vicario, Efraim Reyes, Dolores Badia and Luisa Carrillo
Chapter 7 Organocatalytic Enantioselective Conjugate Additions of Heteroatoms to ?,?Unsaturated Carbonyl Compounds (pages 295–319): Shilei Zhang and Wei Wang
Chapter eight Domino Reactions concerning Catalytic Enantioselective Conjugate Additions (pages 321–350): Lutz F. Tietze and Alexander Dufert
Chapter nine uneven Epoxidations of ?,??Unsaturated Carbonyl Compounds (pages 351–391): Alessandra Lattanzi
Chapter 10 Catalytic uneven Baylis–Hillman Reactions and atmosphere (pages 393–438): Gui?Ling Zhao

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Extra resources for Catalytic Asymmetric Conjugate Reactions

Sample text

Of phosphite L21, 2am underwent a diastereoselective 1,2-addition to furnish the bisphenylated 2amm product as a single diastereoisomer [89]. The use of a monodentate ligand offered the tantalizing possibility to mix different monodentates together to quickly generate combinatorial libraries of complexes. This fascinating approach goes beyond the traditional parallel preparation of modular ligands. Thus, mixtures of monodentate ligands La and Lb can, upon exposure to a transition metal [M], form not only the two homocombinations [M(La )2 ] and [M(La )2 ] but also the heterocombination [M(La )(Lb )].

Ar OH MgX 140a Si Ar Me2 O Si Me 2 141 OH PhMeSiLi 1. LiAlH4 2. 55 142 Si SiMe2Ph Me2 OH OAc 3. Alkyne, Pt cat. Si H 143 Me2 4. NaOH, H2O 140b Si Alkenyl Me2 Regeneration of the tetraorganosilicon reagents 141. In addition to aryl and alkenyl groups, bis(pinacolato)diboron (25) and silyl boronic ester 26 can be used in Rh-cat conjugate additions to transfer boron [49] and silyl groups respectively. 56) [50, 51]. 56 O X SiMe2Ph 144 X = CH2 45%, 96% ee X = O 58%, 96% ee O R1 R2 SiMe2Ph 145 42–72%, 98–99% ee Rh-catalyzed ECA with (pin)B-SiMe2 Ph.

4 1,4-Addition/Enantioselective Protonation So far, the Rh-catalyzed ECA process with β-substituted α,β-unsaturated carbonyl compounds has been reviewed. With this family of substrates, the enantio-determining step is the 1,2-insertion of the acceptor into the Rh–Csp2 bond. 10). 41) [68]. A similar asymmetric transformation has also been reported by Frost and coworkers [165]. This reaction represents a convenient alternative to the synthesis of unnatural phenylalanine derivates (107), which are commonly accessed through Rh-catalyzed asymmetric hydrogenation of β-aryl-α-acetamidoacrylic esters [166].

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Catalytic Asymmetric Conjugate Reactions by Armando Cordova

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