Bauer, D.; Hofmann, K.; Reggelin, M. 2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes. Molecules2023, 28, 7590.
Bauer, D.; Hofmann, K.; Reggelin, M. 2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes. Molecules 2023, 28, 7590.
Bauer, D.; Hofmann, K.; Reggelin, M. 2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes. Molecules2023, 28, 7590.
Bauer, D.; Hofmann, K.; Reggelin, M. 2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes. Molecules 2023, 28, 7590.
Abstract
A rapid synthesis of chiral sulfoxide-functionalized meta-terphenyl derivatives by a 2,5-[C4+C2] ring transformation reaction of pyrylium salts with in-situ generated enantio-merically pure .alpha.-sulfinylacetaldehydes is described. This synthetic method demonstrates for the first time the use of .alpha.-sulfinylacetaldehydes in a reaction sequence initiated by nu-cleophilic attack of pyrylium salts by .alpha.-sulfinylcarbanions to generate chiral aromatic systems. The method presented shows broad applicability starting with various methyl sulfoxides and a number of functionalized pyrylium salts, furnishing meta-terphenyls with complex substitution patterns from readily accessible starting compounds.
Keywords
⍺-sulfinylacetaldehyde; sulfoxide; pyrylium salt; ring transformation; meta-terphenyl
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright:
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