Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction

Scott C. Berk; Robert B. Grossman; Stephen L. Buchwald

doi:10.1021/ja00098a020

Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction

Scott C. Berk
, Robert B. Grossman
, Stephen L. Buchwald

Chemistry

Producción científica: Article › revisión exhaustiva

115 Citas (Scopus)

Resumen

The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp₂Ti(PMe₃)₂ in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

Idioma original	English
Páginas (desde-hasta)	8593-8601
Número de páginas	9
Publicación	Journal of the American Chemical Society
Volumen	116
N.º	19
DOI	https://doi.org/10.1021/ja00098a020
Estado	Published - sept 1 1994

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00098a020

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abstract = "The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol \% of Cp2Ti(PMe3)2 in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.",

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N2 - The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp2Ti(PMe3)2 in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

AB - The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp2Ti(PMe3)2 in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

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Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction

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