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Taming of Thioketones: The First Asymmetric Thia‐Diels–Alder Reaction with Thioketones as Heterodienophiles
Author(s) -
Hejmanowska Joanna,
Jasiński Marcin,
Mlostoń Grzegorz,
Albrecht Łukasz
Publication year - 2017
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.201601307
Subject(s) - enantioselective synthesis , chemistry , aryl , silylation , diels–alder reaction , catalysis , organic chemistry , alkyl
An efficient application of aryl and hetaryl thioketones as dienophiles in the enantioselective thia‐Diels–Alder reaction was explored for the first time. It was found that thioketones could serve as useful heterodienophiles in aminocatalytic, trienamine‐mediated [4+2] cycloadditions with 2,4‐dienals. This enantioselective approach (up to 99:1 er ) was efficiently promoted by diarylprolinol silyl ethers and led to new types of potentially relevant 5,6‐dihydro‐2 H ‐thiopyrans.