(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

Eric M. Woerly, Jonathan E. Miller, Martin D. Burke

Research output: Contribution to journalArticle

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, (1-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 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

Original languageEnglish (US)
Pages (from-to)7732-7740
Number of pages9
JournalTetrahedron
Volume69
Issue number36
DOIs
StatePublished - Sep 9 2013

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Organic Chemistry
Creativity
Alkenes
Molecules
N-methyliminodiacetic acid

Keywords

  • 1,1-Disubstituted boronates
  • 1,1-Disubstituted olefins
  • Iterative cross-coupling
  • MIDA boronates

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry",
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, (1-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 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.",
keywords = "1,1-Disubstituted boronates, 1,1-Disubstituted olefins, Iterative cross-coupling, MIDA boronates",
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T2 - A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry

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AU - Miller, Jonathan E.

AU - Burke, Martin D.

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N2 - 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, (1-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 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

AB - 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, (1-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 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.

KW - 1,1-Disubstituted boronates

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