Bifunctionalized Allenes, Part IX: An Efficient Method for Regioselective Synthesis of 4-Heteroatom-Functionalized Allenecarboxylates

ABSTRACT An efficient method for regioselective synthesis of 4‐heteroatom‐functionalized allenecarboxylates by an atom economical [2,3]‐sigmatropic rearrangement of the mediated 2‐heteroatom‐functionalized alk‐3‐ynecarboxylates is described. Alkyl 4‐(dimethoxyphosphoryl), (diphenylphosphinoyl), (ben...

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Veröffentlicht in:Heteroatom chemistry 2013-07, Vol.24 (4), p.322-331
Hauptverfasser: Ivanov, Ivaylo K., Parushev, Ivaylo D., Christov, Valerij Ch
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Sprache:eng
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Zusammenfassung:ABSTRACT An efficient method for regioselective synthesis of 4‐heteroatom‐functionalized allenecarboxylates by an atom economical [2,3]‐sigmatropic rearrangement of the mediated 2‐heteroatom‐functionalized alk‐3‐ynecarboxylates is described. Alkyl 4‐(dimethoxyphosphoryl), (diphenylphosphinoyl), (benzenesulfinyl), or (methanesulfonyl)‐alka‐2,3‐dienoates can be readily prepared via reactions of alkyl 2‐hydroxy‐alk‐3‐ynoates with dimethylchlorophosphite, chlorodiphenylphosphine, benzensulfanyl chloride, or methanesulfinyl chloride, respectively, in the presence of a base.
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.21096