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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Noncovalent Substrate-Directed Enantioselective Heck Reactions: Synthesis of S- and P-Stereogenic Heterocycles

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de Azambuja, Francisco ; Carmona, Rafaela C. ; Chorro, Tomaz H. D. ; Heerdt, Gabriel ; Correia, Carlos Roque D.
Total Authors: 5
Document type: Journal article
Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 22, n. 32, p. 11205-11209, AUG 1 2016.
Web of Science Citations: 16

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. (AU)

FAPESP's process: 13/10183-5 - Arylation of Cycloalkenes via asymmetric Heck-Matsuda reaction and synthetic applications
Grantee:Rafaela Costa Carmona
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 14/26055-9 - Enantioselective Heck-Matsuda Reaction in non-Symmetric Cyclic Olefins: exploiting the catalyst control over the isomerization
Grantee:Francisco de Azambuja
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support type: Research Projects - Thematic Grants