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Mechanistic Support for Intramolecular Migrative Cyclization of Propargyl Sulfones Provided by Catalytic Asymmetric Induction with a Chiral Counter Cation Strategy
Author(s) -
Yamasaki Kohta,
Yamauchi Akiho,
Inokuma Tsubasa,
Miyakawa Yasunori,
Wang Yinli,
Oriez Raphaël,
Yamaoka Yousuke,
Takasu Kiyosei,
Tanaka Naonobu,
Kashiwada Yoshiki,
Yamada Kenichi
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100274
Subject(s) - chemistry , propargyl , intramolecular force , nucleophile , catalysis , stereochemistry , enantioselective synthesis , asymmetric induction , medicinal chemistry , combinatorial chemistry , organic chemistry
We previously reported an intramolecular migrative cyclization of propargylsufones and sulfonylalkynamides giving oxa‐ and azacycles, respectively. To confirm the postulated reaction mechanism, the reaction was conducted with chiral nucleophiles such as N‐heterocyclic carbenes, phosphines, and pyridines, or with sulfinate anions and chiral cations. As expected, migrative cyclization proceeded to give the enantiomerically enriched products. These results strongly support the postulated mechanism and provide the first example of the asymmetric version of this reaction.