Noncovalent Substrate-Directed Enantioselective Heck Reactions: Synthesis of S- and P-Stereogenic Heterocycles.
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.
Institute of Chemistry, University of Campinas, Campinas, 13083-970, Brazil), Homepage:www.correia-group.com.
Francisco
http://orcid.org/0000-0002-5537-5411
F
de Azambuja
Institute of Chemistry, University of Campinas, Campinas, 13083-970, Brazil), Homepage:www.correia-group.com.
Rafaela C
http://orcid.org/0000-0002-9324-9459
RC
Carmona
Institute of Chemistry, University of Campinas, Campinas, 13083-970, Brazil), Homepage:www.correia-group.com.
Tomaz H D
TH
Chorro
Institute of Chemistry, University of Campinas, Campinas, 13083-970, Brazil), Homepage:www.correia-group.com.
Gabriel
http://orcid.org/0000-0003-4573-0616
G
Heerdt
Institute of Chemistry, University of Campinas, Campinas, 13083-970, Brazil), Homepage:www.correia-group.com. roque@iqm.unicamp.br.
Carlos Roque D
http://orcid.org/0000-0001-5564-6675
CR
Correia
Heck reaction; catalysis; diazonium salts; enantioselectivity; heterocycles