Article
Version 1
Preserved in Portico This version is not peer-reviewed
2,5-[C4+C2] Ringtransformation of Pyrylium Salts with ⍺-Sulfinylacetaldehydes
Version 1
: Received: 27 October 2023 / Approved: 30 October 2023 / Online: 30 October 2023 (06:33:14 CET)
A peer-reviewed article of this Preprint also exists.
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. 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: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Comments (0)
We encourage comments and feedback from a broad range of readers. See criteria for comments and our Diversity statement.
Leave a public commentSend a private comment to the author(s)
* All users must log in before leaving a comment