Domino reactions Tsuji-Trost /Mizoroki-Heck

Scheme 8.63 Domino Tsuji-Trost/Mizoroki-Heck reaction.

In most of the palladium-catalysed domino processes known so far, the Mizoroki-Heck reaction - the palladium(0)-catalysed reaction of aryl halides or triflates as well as of alkenyl halides or triflates with alkenes or alkynes - has been apphed as the starting transformation accordingly to our classification (Table 8.1). It has been combined with another Mizoroki-Heck reaction [6] or a cross-coupling reaction [7], such as Suzuki, Stille or Sonogashira reactions. In other examples, a Tsuji-Trost reaction [8], a carbonylation, a pericyclic or an aldol reaction has been employed as the second step. On the other hand, cross-couphng reactions have also been used as the first step followed by, for example, a Mizoroki-Heck reaction or Tsuji-Trost reactions, palladation of alkynes or allenes [9], carbonylations [10], aminations [11] or palladium(II)-catalysedWacker-type reactions [12] were employed as the first step. A novel illustrative example of the latter procedure is the efficient enantioselective synthesis of vitamin E [13]. 

As part of the total synthesis of the neurotoxin (-(-pumiliotoxin C [69], Minnaard and coworkers [70] used a domino Mizoroki-Heck/Tsuji-Trost reaction as the key step to prepare the perhydroquinoline 124 in 26% yield from 122 and 123 after hydrogenation (Scheme 8.31). Similarly, acyclic tosyl amides with vinyl bromides have been used to give the corresponding lactams in 49-82% yield [71]. 

Tietze, L.R, Redert, T., Bell, H.P. et al. (2008) Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost Heck Mizoroki reaction. Chem. Eur. J., 14, 2527-35. 

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