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Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane

Academic Article
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Overview

related to degree

  • Lira, Ricardo, Ph.D. in Chemistry, Scripps Research , Transferred from University of Michigan with advisor 2005 - 2008

authors

  • Kister, J.
  • DeBaillie, A. C.
  • Lira, Ricardo
  • Roush, William

publication date

  • October 2009

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions with representative aldehydes to give syn-beta-functionalized homoallylic alcohols.

subject areas

  • Alkadienes
  • Alkanes
  • Allyl Compounds
  • Bicyclo Compounds
  • Boranes
  • Kinetics
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2767336

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja905494c

PubMed ID

  • 19775159
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Additional Document Info

start page

  • 14174

end page

  • 14175

volume

  • 131

issue

  • 40

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