Catalytic Asymmetric Conjugate Reactions by Armando Cordova

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By Armando Cordova

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 platforms 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 regarding 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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An examination of the substituent-effect in chiral bicyclo[2 : 2 : 1]heptadiene scaffold revealed that just two methyl groups in ligand L27a are sufficient to impart a high enantioselectivity (95% ee) in the ECA reaction [99]. Moreover, variation of the alkyl group to Bn (L27b), Cy (L27d), allyl (L27f ), and i-Bu (L27e) does not significantly influence the selectivity when compared to L27a [107]; only when moving to a phenyl substituent is a higher ee-value obtained. 0]octadiene (L33) [100, 116] gave high enantiomeric excesses over a wide range of substrates.

The state of the art for asymmetric alkylination methodologies was reviewed in 2009 [204]. 57 Competitive reaction pathways for ECA of alkynes onto α,β-unsaturated compounds. R R 146 148 R R1 Hayashi and coworkers developed three methods to overcome competitive alkyne dimerization in rhodium-catalyzed ECAs of alkynes to enones [205, 206]. 58). This rearrangement was proposed to occur by the formation of rhodium-alkoxide 151, followed by a β-alkyne elimination to form a chiral alkynyl-rhodium complex 152, from which the ECA occurred.

This rearrangement was proposed to occur by the formation of rhodium-alkoxide 151, followed by a β-alkyne elimination to form a chiral alkynyl-rhodium complex 152, from which the ECA occurred. The key to this reaction is that the enone is in the coordination sphere of the rhodium center as the Rh-alkynyl is generated, and that no free alkyne is present during the reaction, thus shutting down the alkyne dimerization pathway. 58). 58 Si(i -Pr)3 155 91%, 97% ee (R ) Rh-catalyzed rearrangement of rac-150 into chiral β-alkynyl ketones.

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