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Efficient one-step aldol-type reaction of ketones with acetals and ketals mediated by dibutylboron triflate/diisopropylethyl amine

Academic Article
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Overview

authors

  • Li, L. S.
  • Das, S.
  • Sinha, Subhash

publication date

  • January 2004

journal

  • Organic Letters  Journal

abstract

  • one-step Mukaiyama aldol type reaction [reaction: see text] A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of beta-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu(2)BOTf and i-Pr(2)NEt affording the products in high yields. Formation of the two possible diastereoisomers of the beta-alkoxy ketones from the chiral acetals shows that the condensation takes place by an S(N)1 mechanism, involving prior opening of the acetal to an oxonium ion.
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol030108u

PubMed ID

  • 14703367
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Additional Document Info

start page

  • 127

end page

  • 130

volume

  • 6

issue

  • 1

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