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

• Published in: Tetrahedron 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
• Language: English
• 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
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.04.021

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]