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|Title:||Noncovalent Substrate-directed Enantioselective Heck Reactions: Synthesis Of S- And P-stereogenic Heterocycles|
Rafaela C.; Chorro
Tomaz H. D.; Heerdt
Carlos Roque D.
|Abstract:||S- and P-Stereogenic heterocycles were synthesized by a remarkably simple enantioselective Heck desymmetrization reaction based on the unprecedented noncovalent directing effect of S=O and P=O functionalities. Selected prochiral symmetric substrates were efficiently arylated using the recently disclosed chiral PyraBOx ligand under mild and open-flask reaction conditions. Several five-membered aryl-sulfones, sulfoxides, and phosphine oxides were synthesized in good to excellent yields, in good to high diastereoselectivity, and enantiomeric ratios up to 98:2. Theoretical calculations also support the noncovalent directing effect of the S=O and P=O functionalities during the arylation process.|
|Editor:||Wiley-V C H Verlag GMBH|
|Citation:||Chemistry-a European Journal. Wiley-v C H Verlag Gmbh, v. 22, p. 11205 - 11209, 2016.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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