Reductive Cyclization of Ester-Containing Enynes with a Practical Titanocene Reagent. Synthesis of Bicyclic Cyclopentenones and Iminocyclopentenes

Robert B. Grossman; Stephen L. Buchwald

doi:10.1021/jo00048a001

Reductive Cyclization of Ester-Containing Enynes with a Practical Titanocene Reagent. Synthesis of Bicyclic Cyclopentenones and Iminocyclopentenes

Robert B. Grossman, Stephen L. Buchwald

Chemistry

Research output: Contribution to journal › Article › peer-review

91 Scopus citations

Abstract

The combination of Cp₂TiCl₂ with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.

Original language	English
Pages (from-to)	5803-5805
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	57
Issue number	22
DOIs	https://doi.org/10.1021/jo00048a001
State	Published - Oct 1 1992

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00048a001

Cite this

@article{09f60f5b300b403fbf22b4ad3b7cd82c,

title = "Reductive Cyclization of Ester-Containing Enynes with a Practical Titanocene Reagent. Synthesis of Bicyclic Cyclopentenones and Iminocyclopentenes",

abstract = "The combination of Cp2TiCl2 with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.",

author = "Grossman, \{Robert B.\} and Buchwald, \{Stephen L.\}",

year = "1992",

month = oct,

day = "1",

doi = "10.1021/jo00048a001",

language = "English",

volume = "57",

pages = "5803--5805",

number = "22",

}

TY - JOUR

T1 - Reductive Cyclization of Ester-Containing Enynes with a Practical Titanocene Reagent. Synthesis of Bicyclic Cyclopentenones and Iminocyclopentenes

AU - Grossman, Robert B.

AU - Buchwald, Stephen L.

PY - 1992/10/1

Y1 - 1992/10/1

N2 - The combination of Cp2TiCl2 with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.

AB - The combination of Cp2TiCl2 with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.

UR - https://www.scopus.com/pages/publications/0001090887

UR - https://www.scopus.com/inward/citedby.url?scp=0001090887&partnerID=8YFLogxK

U2 - 10.1021/jo00048a001

DO - 10.1021/jo00048a001

M3 - Article

AN - SCOPUS:0001090887

SN - 0022-3263

VL - 57

SP - 5803

EP - 5805

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Reductive Cyclization of Ester-Containing Enynes with a Practical Titanocene Reagent. Synthesis of Bicyclic Cyclopentenones and Iminocyclopentenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this