<strong>Matteo Faltracco</strong>
Matteo FaltraccoPhD student
 8/2017 – present
Room:  O|2-4W57
Lab:  O|2-4W19
Phone:
E-mail:  m.a.faltracco@vu.nl

Applications of transition metals-catalysed cascade reactions

The Tsuji-Trost reaction takes an unique position as it constitutes a C-C bond formation between two sp3-sp3 hybridized carbon atoms, potentially resulting in the formation of two new stereocenters. The use of this reaction with (homo)allylic diacetates, allows, after the first allylic displacement, the formation of a second allyl acetate which can undergo a second reaction. This approach has allowed to stereoselectively generate a vinylcyclopropane moiety in a complex system, which could be a key intermediate for the total synthesis of Muironolide A. (figure1)figure1

However, due to the synthetic versability of vinylcyclopropanes, it is possible to envision a much broader field of applications for this methodology, moreover, the presence of a vinyl substituent could control the stereoselectivity of the second π-allylpalladium intermediate and, thereby, of the entire cascade. Among all the possible transformations, it is interesting to explore the cycloisomerization to cyclopentenes, via a diradical or metal-catalyzed mechanism, moreover, the use of nitrones could afford the corresponding tetrahydro-1,2-oxazines through [3+3] cycloaddition, whereas fused cyclopentanes could be obtained via [3+2] cycloaddition with electron poor alkenes in presence of palladium and [4+2] cycloaddition could be achieved with indoles. (figure2)

 figure-2crop