By Armando Cordova
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 related to 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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Additional resources for Catalytic Asymmetric Conjugate Reactions
Because effective coordination of the acceptor to rhodium is crucial for the reaction, acceptors that bear steric bulk in proximity to the unsaturation will be less reactive than unhindered ones. In addition, the activity of Rh/ligand catalytic systems increases with increasing π-accepting properties of the ligand. 3 Other Alkenes The enantioselective construction of stereogenic carbon centers substituted with two aryl groups and one alkyl group is a subject of importance, because this structural motif is often found in pharmaceuticals and natural products.
This trans effect could also explain the high enantioselectivities obtained with mono-substituted chiral diene L29. Chiral tetraﬂuorobenzobarralene L32 was obtained directly from the [4+2] cycloaddition of 1,4-bis((−)-menthoxymethyl)benzene with in situ-generated tetraﬂuorobenzyne, albeit with a low (8%) yield. The resulting diastereoisomers were separated by column chromatography to afford the desired chiral diene . The Ph-dbcot (L37)  and 1,5-Ph-cod (L38)  are achiral dienes, but when coordinated to Rh they become conformationally locked, which leads to a pair of enantiomers that can be subsequently resolved such that, ultimately, enantiomerically pure cationic rhodium complexes [Rh((R)-L37) (MeCN)2 ] (OTf ) and [Rh((R,R)-L38)(MeCN)2 ](BF4 ) can be obtained.
The Rh-hydride subsequently reinserts into the imine enantioselectively, and the Rh-amino bond is then hydrolyzed to generate the reaction product . 43) . 2 eq. 42 Rh-catalyzed conjugate addition/enantioselective protonation using guaiacol of the sole proton source. ) O O PGN OR Ar 116 13 examples 16 – 93%, 63 – 91% ee Applications of Rh-catalyzed addition/enantioselective protonation. these examples the choice of the additional proton source (phenol 110, boric acid (B(OH)3 ), or phthalimide 115) was critical to obtain high yields and good selectivities.
Catalytic Asymmetric Conjugate Reactions by Armando Cordova