Reactions of α‑Functionally Substituted Enals with Terminal Alkynes: Unexpected Assembly of 2‑Amino-2-Cyclopentenones

Reactions of α‑Functionally Substituted Enals with Terminal Alkynes: Unexpected Assembly of 2‑Amino-2-Cyclopentenones

The reactions of α-chalcogen, α-halo, or α-amino functionally substituted enals with terminal alkynes leading either to corresponding propargyl alcohols (for O-, S-, Cl-, and Br-bearing substrates) or unexpected 2-amino-2-cyclopentenones (for aminoenals) are described. The key feature of these react...

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Veröffentlicht in:Journal of organic chemistry 2023-04, Vol.88 (7), p.4886-4890
Hauptverfasser: Shnigirev, Rustam B., Ushakov, Igor A., Semenov, Valentin A., Rulev, Alexander Yu
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container_issue 7
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container_title Journal of organic chemistry
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creator Shnigirev, Rustam B.
Ushakov, Igor A.
Semenov, Valentin A.
Rulev, Alexander Yu
description The reactions of α-chalcogen, α-halo, or α-amino functionally substituted enals with terminal alkynes leading either to corresponding propargyl alcohols (for O-, S-, Cl-, and Br-bearing substrates) or unexpected 2-amino-2-cyclopentenones (for aminoenals) are described. The key feature of these reactions is the rearrangement of adducts bearing amino groups on silica gel that triggered further cyclization to five-membered carbocycles.
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title Reactions of α‑Functionally Substituted Enals with Terminal Alkynes: Unexpected Assembly of 2‑Amino-2-Cyclopentenones
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