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

Eric M. Woerly; Justin R. Struble; Nagarjuna Palyam; Sean P. O'Hara; Martin D. Burke

doi:10.1016/j.tet.2011.04.021

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

Eric M. Woerly, Justin R. Struble, Nagarjuna Palyam, Sean P. O'Hara, Martin D. Burke

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

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.

Original language	English (US)
Pages (from-to)	4333-4343
Number of pages	11
Journal	Tetrahedron
Volume	67
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2011.04.021
State	Published - Jun 17 2011

Keywords

Iterative cross-coupling
MIDA boronates
Polyene natural products
cis-Alkenes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.04.021

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title = "(Z)-(2-bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis",

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.",

keywords = "Iterative cross-coupling, MIDA boronates, Polyene natural products, cis-Alkenes",

author = "Woerly, {Eric M.} and Struble, {Justin R.} and Nagarjuna Palyam and O'Hara, {Sean P.} and Burke, {Martin D.}",

note = "Funding Information: We gratefully acknowledge the NIH for funding ( R01 GM080436 ). E.M.W. is an NSF Graduate Fellow and M.D.B. is an Early Career Scientist of the Howard Hughes Medical Institute.",

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T2 - A readily accessible and highly versatile building block for small molecule synthesis

AU - Woerly, Eric M.

AU - Struble, Justin R.

AU - Palyam, Nagarjuna

AU - O'Hara, Sean P.

AU - Burke, Martin D.

N1 - Funding Information: We gratefully acknowledge the NIH for funding ( R01 GM080436 ). E.M.W. is an NSF Graduate Fellow and M.D.B. is an Early Career Scientist of the Howard Hughes Medical Institute.

PY - 2011/6/17

Y1 - 2011/6/17

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, (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 - 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.

KW - Iterative cross-coupling

KW - MIDA boronates

KW - Polyene natural products

KW - cis-Alkenes

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

Abstract

Keywords

ASJC Scopus subject areas

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