Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 7, Pages 1828-1834Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100274
Keywords
sulfonyl migration; cyclization; organocatalyst; asymmetric reaction; catalytic reaction
Categories
Funding
- JSPS [JP18K06579, JP20K06965]
- Tokushima University [1802001]
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The study confirmed an enantioselective intramolecular migrative cyclization reaction, where the use of chiral nucleophiles led to enantiomerically enriched products.
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.
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