[Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions

Brandon L. Ashfeld; Kenneth A. Miller; Anna J. Smith; Kristy Tran; Stephen F. Martin

doi:10.1021/ol0504300

[Rh(CO)₂Cl]₂-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions

Brandon L. Ashfeld, Kenneth A. Miller, Anna J. Smith, Kristy Tran, Stephen F. Martin

Penn State Brandywine

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

39 Scopus citations

Abstract

(Chemical Equation Presented) Three novel domino reaction processes have been discovered and developed that employ the regioselective and stereoselective [Rh(CO)₂Cl]₂-catatyzed alkylations of allylic trifluoroacetates with α-substituted sodiomalonates followed by an intramolecular Pauson-Khand annulation, a [5 + 2] cycloaddition, or a cycloisomerization. A unique aspect of the methodology is that a single catalyst is used to effect sequential transformations simply by increasing the temperature for the second reaction.

Original language	English (US)
Pages (from-to)	1661-1663
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	8
DOIs	https://doi.org/10.1021/ol0504300
State	Published - Apr 14 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0504300

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abstract = "(Chemical Equation Presented) Three novel domino reaction processes have been discovered and developed that employ the regioselective and stereoselective [Rh(CO)2Cl]2-catatyzed alkylations of allylic trifluoroacetates with α-substituted sodiomalonates followed by an intramolecular Pauson-Khand annulation, a [5 + 2] cycloaddition, or a cycloisomerization. A unique aspect of the methodology is that a single catalyst is used to effect sequential transformations simply by increasing the temperature for the second reaction.",

author = "Ashfeld, {Brandon L.} and Miller, {Kenneth A.} and Smith, {Anna J.} and Kristy Tran and Martin, {Stephen F.}",

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T1 - [Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions

AU - Ashfeld, Brandon L.

AU - Miller, Kenneth A.

AU - Smith, Anna J.

AU - Tran, Kristy

AU - Martin, Stephen F.

PY - 2005/4/14

Y1 - 2005/4/14

N2 - (Chemical Equation Presented) Three novel domino reaction processes have been discovered and developed that employ the regioselective and stereoselective [Rh(CO)2Cl]2-catatyzed alkylations of allylic trifluoroacetates with α-substituted sodiomalonates followed by an intramolecular Pauson-Khand annulation, a [5 + 2] cycloaddition, or a cycloisomerization. A unique aspect of the methodology is that a single catalyst is used to effect sequential transformations simply by increasing the temperature for the second reaction.

AB - (Chemical Equation Presented) Three novel domino reaction processes have been discovered and developed that employ the regioselective and stereoselective [Rh(CO)2Cl]2-catatyzed alkylations of allylic trifluoroacetates with α-substituted sodiomalonates followed by an intramolecular Pauson-Khand annulation, a [5 + 2] cycloaddition, or a cycloisomerization. A unique aspect of the methodology is that a single catalyst is used to effect sequential transformations simply by increasing the temperature for the second reaction.

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

[Rh(CO)₂Cl]₂-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions

Abstract

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