( Z)-(2-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, ( Z)-(2-bromovinyl)- N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule s...

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Published inTetrahedron Vol. 67; no. 24; pp. 4333 - 4343
Main Authors Woerly, Eric M., Struble, Justin R., Palyam, Nagarjuna, O’Hara, Sean P., Burke, Martin D.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.06.2011
Elsevier
Subjects
Accessibility
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
cis-Alkenes
Construction
Cross coupling
Iterative cross-coupling
MIDA boronates
organic compounds
Physical Sciences
Platforms
Polyene natural products
Science & Technology
Synthesis (chemistry)
Tetrahedrons
cis-Alkenes
Iterative cross-coupling
Polyene natural products
MIDA boronates
SOLID-PHASE SYNTHESIS
ACIDS
STRATEGY
TUBULIN POLYMERIZATION
VINYL HALIDES
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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Abstract Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, ( Z)-(2-bromovinyl)- N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of cis-alkene-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various cis-olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform. [Display omitted]
AbstractList Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (Z)-(2-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of cis-alkene-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various cis-olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform. (C) 2011 Elsevier Ltd. All rights reserved.
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, ( Z)-(2-bromovinyl)- N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of cis-alkene-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various cis-olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform. [Display omitted]
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (Z)-(2-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of cis-alkene-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various cis-olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (Z)-(2-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of cis-alkene-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various cis-olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform. AB:
Author O’Hara, Sean P.
Woerly, Eric M.
Palyam, Nagarjuna
Struble, Justin R.
Burke, Martin D.
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Issue 24
Keywords cis-Alkenes
Iterative cross-coupling
Polyene natural products
MIDA boronates
SOLID-PHASE SYNTHESIS
ACIDS
STRATEGY
TUBULIN POLYMERIZATION
VINYL HALIDES
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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SSID ssj0001123
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Snippet Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small...
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SubjectTerms Accessibility
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
cis-Alkenes
Construction
Cross coupling
Iterative cross-coupling
MIDA boronates
organic compounds
Physical Sciences
Platforms
Polyene natural products
Science & Technology
Synthesis (chemistry)
Tetrahedrons
Title ( Z)-(2-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis
URI https://dx.doi.org/10.1016/j.tet.2011.04.021
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