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

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112 Scopus citations

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.

Original language	English
Pages (from-to)	8593-8601
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	116
Issue number	19
DOIs	https://doi.org/10.1021/ja00098a020
State	Published - Sep 1 1994

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction",

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.",

author = "Berk, {Scott C.} and Grossman, {Robert B.} and Buchwald, {Stephen L.}",

year = "1994",

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AU - Berk, Scott C.

AU - Grossman, Robert B.

AU - Buchwald, Stephen L.

PY - 1994/9/1

Y1 - 1994/9/1

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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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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

Abstract

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