Artículos de revistas
Noncovalent Substrate-directed Enantioselective Heck Reactions: Synthesis Of S- And P-stereogenic Heterocycles
Registro en:
Chemistry-a European Journal. Wiley-v C H Verlag Gmbh, v. 22, p. 11205 - 11209, 2016.
0947-6539
1521-3765
WOS:000382918700017
10.1002/chem.201602572
Autor
de Azambuja
Francisco; Carmona
Rafaela C.; Chorro
Tomaz H. D.; Heerdt
Gabriel; Correia
Carlos Roque D.
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) 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. 22 32 11205 11209 Sao Paulo Research Foundation (FAPESP) [2014/25770-6, 2013/07600-3, 2014/26055-9, 2013/10183-5] Brazilian National Research Council (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)