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Type: Artigo
Title: Noncovalent Substrate-directed Enantioselective Heck Reactions: Synthesis Of S- And P-stereogenic Heterocycles
Author: de Azambuja
Francisco; Carmona
Rafaela C.; Chorro
Tomaz H. D.; Heerdt
Gabriel; Correia
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.
Subject: Catalysis
Diazonium Salts
Heck Reaction
Editor: Wiley-V C H Verlag GMBH
Citation: Chemistry-a European Journal. Wiley-v C H Verlag Gmbh, v. 22, p. 11205 - 11209, 2016.
Rights: fechado
Identifier DOI: 10.1002/chem.201602572
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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