Mannich vinylogous Mukaiyama

Vinylogous Mukaiyama Mannich Reactions of Silyl Dienolates 159... 

Vinylogous Mukaiyama Mannich Reactions of Silyl Dienolates I 165 Table 5.4 Brens ted acid catalyzed vinylogous Mannich reaction according to Akiyama et al. [10],... 

New Au(III)-pyridine-2-carboxylate complexes were developed to catalyze the intramolecular reaction between furan and acetylene to form phenols <04AE(G)6545>. These pre-catalysts provide higher reaction conversion than AuClj. The Lewis acid catalyzed vinylogous Mukaiyama-Mannich addition of trimethylsilyloxyfuran to aldimines, that generates 6-amino-Y-butenolide intermediates, was applied to the synthesis of piperidines... 

Giera DS, Sickert M, Schneider C (2009) A Straightforward Synthesis of (5)-Anabasine via the Catalytic, Enantioselective Vinylogous Mukaiyama-Mannich Reaction. Synthesis 3797... 

Vinylogous Mukaiyama Mannich Reactions with Br0nsted Add Catalysis... 

In this review we will attempt to highlight the most important contributions toward the realization of a catalytic, enantioselective, vinylogous Mannich reaction and show the current state of the art. This chapter is organized in such a way that vinylogous Mannich reactions of preformed silyl dienolates in Mukaiyama type reactions will be discussed first followed by direct vinylogous Mannich reactions of unmodified substrates. 

The catalytic, enantioselective, vinylogous Mannich reaction has recently emerged as a very powerful tool in organic synthesis for the assembly of highly functionalized and optically enriched 6 amino carbonyl compounds. Two distinctly different strategies have been developed. The first approach calls for the reaction of preformed silyl dienolates as latent metal dienolates that react in a chiral Lewis acid or Bronsted acid catalyzed Mukaiyama type reaction with imines. Alternatively, unmodified CH acidic substrates such as a,a dicyanoalkenes or 7 butenolides were used in vinylo gous Mannich reactions that upon deprotonation with a basic residue in the catalytic system generate chiral dienolates in situ. 

Activation of C=N Double Bonds. TBDMS triflate has been used to promote additions to, and for the isomerization of, a number of systems containing carbon-nitrogen double bonds. TBDMS triflate is the optimal silyl triflate to promote the Mukaiyama-type vinylogous imino-aldol (Mannich-type) addition of 2-[(f-butyldimethylsilyl)oxy]furan to the IV-benzyl imine derived from (25)-2,3-0-isopropylideneglyceraldehyde (eq 36). ... 

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