3 years ago

Torquoselective Mechanochemical Activation of the Staudinger Reaction To Form β-Lactams

Torquoselective Mechanochemical
Activation of the
Staudinger Reaction To Form β-Lactams
María Isabel Menéndez, Dominik Marx
The Staudinger reaction yielding β-lactam rings via [2 + 2] cycloaddition is a torquoselective reaction where the stereochemistry of the product can be steered by suitable substituents. Although the mechanochemical ring-opening of β-lactams has been investigated recently, the force-assisted synthesis of this important functional four-ring motif remains unexplored. As it will be computationally demonstrated, mechanochemical activation greatly reduces the barrier of the rate-limiting ring-closure step while, at the same time, preserves its torquoselectivity. This finding strongly suggests that strained four-membered rings can be readily incorporated in chain molecules using sonication techniques that greatly enhance reactivity while conserving selectivity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03036

DOI: 10.1021/acs.joc.7b03036

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