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One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf

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C. Wade Downey,* Miles W. Johnson, and Kathryn J. Tracy

Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173 wdowney@richmond.edu

J. Org. Chem., 2008, 73 (8), pp 3299–3302

DOI: 10.1021/jo8001084

Publication Date (Web): March 12, 2008

Abstract

Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.

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This article has been cited by 5 ACS Journal articles (5 most recent appear below).

Nickel(0)-Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis
Danielle M. Shacklady-McAtee, Srimoyee Dasgupta, and Mary P. Watson
Organic Letters2011 13 (13), 3490-3493
- Nickel(0)-Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis
  Danielle M. Shacklady-McAtee, Srimoyee Dasgupta, and Mary P. Watson
  Organic Letters2011 13 (13), 3490-3493
  A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate
C. Wade Downey, Miles W. Johnson, Daniel H. Lawrence, Alan S. Fleisher and Kathryn J. Tracy
The Journal of Organic Chemistry2010 75 (15), 5351-5354
- Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate
  C. Wade Downey, Miles W. Johnson, Daniel H. Lawrence, Alan S. Fleisher and Kathryn J. Tracy
  The Journal of Organic Chemistry2010 75 (15), 5351-5354
  In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to proceed via a three-step, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions
Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
The Journal of Organic Chemistry2010 75 (4), 1077-1086
- Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions
  Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
  The Journal of Organic Chemistry2010 75 (4), 1077-1086
  It has been widely accepted that both the protection of carbonyls and the deprotection of acetals and ketals involve the participation of a water molecule: formation of acetals and ketals is a dehydration process, whereas the deprotection is often ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
C. Wade Downey, Brian D. Mahoney and Vincent R. Lipari
The Journal of Organic Chemistry2009 74 (7), 2904-2906
- Trimethylsilyl Trifluoromethanesulfonate- Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
  C. Wade Downey, Brian D. Mahoney and Vincent R. Lipari
  The Journal of Organic Chemistry2009 74 (7), 2904-2906
  In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
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Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension
Claudio Curti, Andrea Sartori, Lucia Battistini, Gloria Rassu, Paola Burreddu, Franca Zanardi and Giovanni Casiraghi
The Journal of Organic Chemistry2008 73 (14), 5446-5451
- Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension
  Claudio Curti, Andrea Sartori, Lucia Battistini, Gloria Rassu, Paola Burreddu, Franca Zanardi and Giovanni Casiraghi
  The Journal of Organic Chemistry2008 73 (14), 5446-5451
  A vinylogous, silylative, and direct variant of the venerable Mukaiyama aldol reaction has been developed. Exploiting N-Boc-pyrrol-2(5H)-one as the conjugate donor, several aldehyde and ketone acceptors were scrutinized under the guidance of suitable ...
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