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Enantioselective Synthesis of Spiro[1,3‐indanedione–tetrahydrothiophene]s by Organocatalytic Sulfa‐Michael/Michael Domino Reaction
Author(s) -
Duan Jindian,
Cheng Jing,
Li Bing,
Qi Fei,
Li Pengfei
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500837
Subject(s) - tetrahydrothiophene , michael reaction , chemistry , domino , enantioselective synthesis , thiourea , aldol reaction , organic chemistry , organocatalysis , stereocenter , medicinal chemistry , catalysis
The organocatalytic asymmetric domino reaction between 2‐arylidene‐1,3‐indanediones and 4‐mercapto‐2‐butenoates for the construction of chiral spiro[indane‐1,3‐dione–tetrahydrothiophene] skeletons was developed. In the presence of a tertiary amine–thiourea organocatalyst, a series of 2‐arylidene‐1,3‐indanediones reacted with tert ‐butyl 4‐mercapto‐2‐butenoate smoothly to furnish chiral spiro heterocycles in good yields (75–99 %) with high enantioselectivities (89–99 % ee ) and diastereoselectivities (75.4:24.6 to 97.1:2.9 dr ). Notably, functionalized chiral spiro heterocycles were also built in one pot through an aldol condensation/sulfa‐Michael/Michael domino reaction in similarly high yields with high asymmetric induction.