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Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences

Academic Article
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Overview

related to degree

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

authors

  • Chen, Ming
  • Handa, M.
  • Roush, William

publication date

  • October 2009

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The hydroboration of allene 7 with ((d)Ipc)(2)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >or=12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.

subject areas

  • Alcohols
  • Aldehydes
  • Alkadienes
  • Boron
  • Stereoisomerism
  • Substrate Specificity
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Identity

PubMed Central ID

  • PMC2762002

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja904599h

PubMed ID

  • 19778012
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Additional Document Info

start page

  • 14602

end page

  • 14603

volume

  • 131

issue

  • 41

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