Catalytic Asymmetric Conjugate Reactions by Armando Cordova

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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The effective construction of chiral quaternary carbons is arguably one of the biggest challenges in asymmetric catalysis [148–150]. 32 O N t -Bu Ph O 76: dr = 96:4 major: 92% yield 99% ee Transfer of the axial chirality of 73m. 33 Influence of the ligand on the regioselectivity of Rh-catalyzed ECA onto maleimides. of ECA to β,β-disubstituted α,β-unsaturated carbonyl compounds [149]. 33) [151]. Whereas, Rh/(H8 -binap)-catalyzed processes give rise preferably to 1,4-adducts 78 with a quaternary stereogenic center, the Rh/((R,R)-L28a) catalyst leads to cis/trans mixtures of 79.

2 Rh-Catalyzed ECA of Organoboron Reagents O CHO 1. H OH 2. 18 Tandem Rh-catalyzed ECA with PhB(9-BBN) onto 2-cyclohexenone. 19 Reaction pathways in the Rh-catalyzed conjugate addition of arylboronic acids to enals. 19). 20 [137]. Whereas, the use of phosphines ligands in the addition of phenylboronic acid to cinnamaldehyde 31a led selectively to the allyl alcohol 34am, the Rh/diene-catalyzed process resulted in the formation of the desired 1,4-adduct 32am. The use of chiral dienes (L30f, L27b, and L28b) was optimal for the formation of a wide range of enantiomerically enriched 3,3-diarylpropanals and 3-arylalkanals.

Onto β-silyl α,β-unsaturated ketones [104]. 2]octadiene framework with an aryl moiety (L29) was necessary to achieve high enantioselectivities [44, 103]. , 2,6-Me2 C6 H3 ) were found to be important to achieve highest selectivities. 17 18 1 Rhodium- and Palladium-Catalyzed Asymmetric Conjugate Additions The lengthy synthesis of L27 and the need to resolve L28, L34, L35, and L36 by preparative high-performance liquid chromatography (HPLC) has impeded the widespread investigation of chiral dienes.

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