Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate

Abstract Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-arylhydroxyacetone enolate.

[1]  S. Denmark,et al.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones. , 2003, Chemical reviews.

[2]  M. Yus,et al.  Diastereoselective allylation of carbonyl compounds and imines: application to the synthesis of natural products. , 2013, Chemical reviews.

[3]  M. Lombardo,et al.  A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF. , 2001, Organic letters.

[4]  M. Lombardo,et al.  An environmentally friendly α-hydroxyallylation reaction of the Garner aldehyde: a comparative assessment of alternative Barbier conditions , 2004 .

[5]  R. Heck,et al.  Palladium-catalyzed conjugated diene synthesis from vinylic halides and olefinic compounds , 1975 .

[6]  R. Heck.  Palladium‐Catalyzed Vinylation of Organic Halides , 2005 .

[7]  Veselin Maslak,et al.  A useful synthetic equivalent of an acetone enolate , 2009 .

[8]  A. Whiting,et al.  The Heck-Mizoroki cross-coupling reaction: a mechanistic perspective. , 2007, Organic & biomolecular chemistry.

[9]  R. Madsen,et al.  Chain elongation of aldoses by indium-mediated coupling with 3-bromopropenyl esters. , 2005, The Journal of organic chemistry.

[10]  Thomas G Minehan,et al.  Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides. , 2010, Tetrahedron letters.

[11]  Chao-Jun Li,et al.  Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. , 2005, Chemical reviews.

[12]  C. Bruneau,et al.  Stereoselective preparation of Z-trisubstituted alkylidene cyclic carbonates via palladium-catalyzed carboncarbon bond formation , 2000 .

[13]  T. Jeffery.  ON THE EFFICIENCY OF TETRAALKYLAMMONIUM SALTS IN HECK TYPE REACTIONS , 1996 .

[14]  M. Lombardo,et al.  α-Hydroxyallylation Reaction of Carbonyl Compounds , 2007 .

[15]  I. Beletskaya,et al.  Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction , 2005 .

[16]  Chao-Jun Li,et al.  Organic syntheses using indium-mediated and catalyzed reactions in aqueous media , 1999 .

[17]  Vladimir Divjakovic,et al.  A useful synthetic equivalent of a hydroxyacetone enolate. , 2011, Organic letters.

[18]  V. Nair,et al.  Indium- and gallium-mediated carbon-carbon bond-forming reactions in organic synthesis , 2004 .

[19]  M. Lombardo,et al.  An efficient high-yield synthesis of D-ribo-phytosphingosine. , 2006, Organic letters.

[20]  I. Beletskaya,et al.  The heck reaction as a sharpening stone of palladium catalysis. , 2000, Chemical reviews.

[21]  T. Loh,et al.  Organoindium reagents: the preparation and application in organic synthesis. , 2013, Chemical reviews.

[22]  H. Akita,et al.  Total synthesis of (+)-asperlin , 2008 .