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Type: Outro documento
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: Catálise
Sais de diazônio
Reação de Heck
Country: Alemanha
Editor: Wiley
Rights: Fechado
Identifier DOI: 10.1002/chem.201602572
Date Issue: 2016
Appears in Collections:IQ - Artigos e Outros Documentos

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