Chirality transfer in the synthesis of 2,3-dihydro-1,4-dithiine derivatives

Wojciech J. Depa , Natalia Buszta , Piotr Guńka , Janusz Zachara , Agata Bajek-Bil , Grażyna Groszek

Abstract

A new method for the synthesis of chiral 2,3-dihydro-1,4-dithiine derivatives that involves a reaction of chiral cyclic aliphatic dithioacetal in the presence of Lewis acid has been developed. The title product contains a 1,4-dithiane substituent with two stereogenic centers. The presence of a stereogenic center in the α position to the cyclic dithioacetal substrate controls the stereogenicity of two centers in the newly formed molecule whose absolute configuration is defined. The mechanism based on chirality transfer process was proposed.
Author Wojciech J. Depa
Wojciech J. Depa,,
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, Natalia Buszta
Natalia Buszta,,
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, Piotr Guńka (FC / CofIC)
Piotr Guńka,,
- Chair Of Inorganic Chemistry
, Janusz Zachara (FC / CofIC)
Janusz Zachara,,
- Chair Of Inorganic Chemistry
, Agata Bajek-Bil
Agata Bajek-Bil,,
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, Grażyna Groszek
Grażyna Groszek,,
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Journal seriesSynthetic Communications, ISSN 0039-7911, e-ISSN 1532-2432
Issue year2020
Pages1-7
Publication size in sheets0.5
ASJC Classification1605 Organic Chemistry
DOIDOI:10.1080/00397911.2020.1801746
Languageen angielski
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 40.0, 25-08-2020, ArticleFromJournal
Publication indicators Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.392; WoS Impact Factor: 2018 = 1.439 (2) - 2018=1.407 (5)
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