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Catalyst-dependent selectivity in sulfonium ylide cycloisomerization reactions.


ABSTRACT: Divergent catalysis is an emerging field whereby access to structurally diverse compounds from a common precursor is achieved through controlled reaction pathways. Herein we present an unusual example of ?-acid catalyst dependent selectivity in the cycloisomerization of alkene-tethered sulfonium ylides. Computational mechanistic studies revealed how the ability of palladium to cycle through oxidation states largely controls the selectivity.

SUBMITTER: Oost R 

PROVIDER: S-EPMC6137435 | biostudies-other | 2018 Sep

REPOSITORIES: biostudies-other

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Catalyst-dependent selectivity in sulfonium ylide cycloisomerization reactions.

Oost Rik R   Neuhaus James D JD   Misale Antonio A   Meyrelles Ricardo R   Veiros Luís F LF   Maulide Nuno N  

Chemical science 20180725 35


Divergent catalysis is an emerging field whereby access to structurally diverse compounds from a common precursor is achieved through controlled reaction pathways. Herein we present an unusual example of π-acid catalyst dependent selectivity in the cycloisomerization of alkene-tethered sulfonium ylides. Computational mechanistic studies revealed how the ability of palladium to cycle through oxidation states largely controls the selectivity. ...[more]

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