Open AccessPalladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides
Author(s) -
Gillian Laidlaw,
Vilius Franckevičius
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c04075
Subject(s) - stereocenter , tsuji–trost reaction , chemistry , palladium , catalysis , alkylation , sulfonyl , allylic rearrangement , combinatorial chemistry , enantioselective synthesis , organic chemistry , alkyl
A palladium-catalyzed decarboxylative asymmetric allylic alkylation of thietane 1,1-dioxides via linear enolate intermediates from racemic starting materials has been developed. This process installs an α-sulfonyl tetrasubstituted stereogenic center with high enantioselectivity. The potential to transform the alkylated products to novel types of enantioenriched spirocycles for medicinal chemistry applications has also been demonstrated.