Chiral Bicyclic Guanidine-Catalyzed
Enantioselective
Sulfenylation of Oxindoles and Benzofuran-2(3<i>H</i>)‑ones
Lisha Huang
Jiangtao Li
Yan Zhao
Xinyi Ye
Yang Liu
Lin Yan
Choon-Hong Tan
Hongjun Liu
Zhiyong Jiang
10.1021/acs.joc.5b01606.s002
https://acs.figshare.com/articles/dataset/Chiral_Bicyclic_Guanidine_Catalyzed_Enantioselective_Sulfenylation_of_Oxindoles_and_Benzofuran_2_3_i_H_i_ones/2134795
A chiral
bicyclic guanidine-catalyzed enantioselective sulfenylation
of 3-substituted oxindoles to <i>N</i>-(sulfanyl)succinimides
has been developed. A series of unprecedented 3-sulfenylated oxindoles,
such as 3-benzyl/alkyl-substituted 3-benzyl/alkyloxindoles, were obtained
with high enantioselectivities (up to 98% ee). This methodology is
also effective for the first asymmetric sulfenylation of benzofuran-2(3<i>H</i>)-ones, providing 3-benzyl-3-benzylthio-substituted benzofuran-2(3<i>H</i>)-ones with satisfactory results (up to 95% ee).
2015-09-04 00:00:00
ee
benzofuran
oxindole
sulfenylation
benzyl