Mukaiyama amide coupling

In 1989, Isayama and Mukaiyama reported a related Co-catalyzed coupling reaction that employs a,b-unsaturated nitriles, amides, and esters with PhSiLb as a hydrogen source [9]. Cobalt-bis(diketonato) complex, Co(II)(dpm)2 [dpm = bis(dipivaloylmethanato)] (5mol%), exhibited high catalytic activity at 20 °C in the coupling of excess acrylonitrile and ben-zaldehyde to provide b-hydroxy nitrile 4 in 93% yield (syn anti = 50 50) (Scheme 5). N,N-Dimethylacrylamide and methyl cinnamate both reacted... 

The first use of a polymer-supported Mukaiyama reagent for microwave-mediated synthesis of amides was presented in 2004 [125]. To prove its effectiveness, even in difficult coupling reactions, it was used in the microwave-accelerated synthesis of an amide from sterically hindered pivalic acid (Scheme 16.83). The mixture was subjected to microwave irradiation at 100 °C for 10 min and the desired product was obtained in 80% yield. 

Mukaiyama s tridentate diamino alcohol 6 is derived from the coupling of two L-proline units followed by reduction of the ester/amide carbonyl groups ent-6... 

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