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Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration

Academic Article
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Overview

related to degree

  • Chen, Ming, Ph.D. in Organic Chemistry, Scripps Research 2007 - 2012

authors

  • Han, J. L.
  • Chen, Ming
  • Roush, William

publication date

  • June 2012

journal

  • Organic Letters  Journal

abstract

  • Enantioselective hydroboration of racemic allenylboronate (±)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 °C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 °C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 °C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.

subject areas

  • Aldehydes
  • Boric Acids
  • Boron Compounds
  • Heterocyclic Compounds, 1-Ring
  • Hydrogenation
  • Kinetics
  • Methylation
  • Molecular Structure
  • Stereoisomerism
  • Thermodynamics
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Identity

PubMed Central ID

  • PMC3426628

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol3010968

PubMed ID

  • 22646839
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Additional Document Info

start page

  • 3028

end page

  • 3031

volume

  • 14

issue

  • 12

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