Literature DB >> 17406488

Triflimide (HNTf2)-catalyzed aldehyde cross-aldol reaction using "super silyl" enol ethers.

Matthew B Boxer1, Hisashi Yamamoto.   

Abstract

The synthesis of the acetaldehyde-derived tris(trimethylsilyl)silyl (super silyl) enol ether is described, as well as its use in the high-yielding aldehyde cross-aldol reaction. The super silyl enol ether shows unprecedented reactivity in giving the 1:1 adduct in very high yield. This reaction is catalyzed by 0.05 mol% of the Brønsted acid triflimide (HNTf2) and is complete within 15 min, making the protocol very attractive for large-scale synthesis.

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Year:  2006        PMID: 17406488     DOI: 10.1038/nprot.2006.389

Source DB:  PubMed          Journal:  Nat Protoc        ISSN: 1750-2799            Impact factor:   13.491


  5 in total

1.  Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors:  Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

2.  Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Org Lett       Date:  2013-11-08       Impact factor: 6.005

3.  Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement.

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

4.  A triple-aldol cascade reaction for the rapid assembly of polyketides.

Authors:  Brian J Albert; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

5.  β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Authors:  Jakub Saadi; Hisashi Yamamoto
Journal:  Chemistry       Date:  2013-02-19       Impact factor: 5.236

  5 in total

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