[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

41 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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title = "[Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions",

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.\}",

year = "2005",

month = apr,

day = "14",

doi = "10.1021/ol0504300",

language = "English (US)",

volume = "7",

pages = "1661--1663",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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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.

UR - https://www.scopus.com/pages/publications/17844405274

UR - https://www.scopus.com/pages/publications/17844405274#tab=citedBy

U2 - 10.1021/ol0504300

DO - 10.1021/ol0504300

M3 - Article

C2 - 15816777

AN - SCOPUS:17844405274

SN - 1523-7060

VL - 7

SP - 1661

EP - 1663

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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