Recent Developments in Asymmetric Hetero-Diels-Alder Reactions of Dithioesters

Abstract Recent studies dealing with asymmetric thia-Diels-Alder reactions of dithioesters as heterodienophiles are described. A diastereoselective version involving new chiral dithioesters and the first example of a catalytic enantioselective version are described. The absolute stereochemistry of the cycloadducts was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction observed experimentally, stereochemical models for Cu(II)/BOX/dithioester complexes are proposed. GRAPHICAL ABSTRACT

[1]  I. Chataigner,et al.  Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters , 2012 .

[2]  G. Desimoni,et al.  Update 1 of: C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis. , 2011, Chemical reviews.

[3]  I. Chataigner,et al.  First catalytic enantioselective version of a thia hetero-Diels–Alder reaction with dithioesters , 2010 .

[4]  Yu. G. Shermolovich,et al.  Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates , 2010 .

[5]  H. Pellissier Asymmetric Hetero‐Diels—Alder Reactions of Carbonyl Compounds , 2009 .

[6]  C. Barner‐Kowollik,et al.  Ultrafast click conjugation of macromolecular building blocks at ambient temperature. , 2009, Angewandte Chemie.

[7]  J. Cossy,et al.  Copper-catalyzed Diels-Alder reactions. , 2008, Chemical reviews.

[8]  C. Barner‐Kowollik,et al.  An atom-efficient conjugation approach to well-defined block copolymers using RAFT chemistry and hetero Diels-Alder cycloaddition. , 2008, Chemical communications.

[9]  K. Jørgensen,et al.  Bisoxazoline-Lewis acid-catalyzed direct-electron demand oxo-hetero-Diels-Alder reactions of N-oxy-pyridine aldehyde and ketone derivatives. , 2007, The Journal of organic chemistry.

[10]  A. Gaumont,et al.  Pyridinedithioesters as heterodienophiles: application to the synthesis of aprikalim. , 2006, Organic letters.

[11]  C. Philouze,et al.  A Hetero‐Diels−Alder Approach to Phosphonothiashikimic Acid and New Thiaglycosides , 2004 .

[12]  E. Corey Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications. , 2002, Angewandte Chemie.

[13]  S. Masson,et al.  Synthesis of thiapyranoside precursors using the building-block approach from a phosphonodifluorodithioacetate , 2002 .

[14]  P. Leung,et al.  Organopalladium complex promoted asymmetric hetero Diels-Alder reactions between a thiocarbonyl dienophile and a phospha-substituted cyclic diene , 2002 .

[15]  M. Heras,et al.  First synthesis of a phosphonothiashikimic acid derivative , 2001 .

[16]  M. Heras,et al.  Phosphonodithioformates as heterodienophiles: synthesis of (3,6-dihydro-2H-thiopyran-2-yl)phosphonates , 2000 .

[17]  Scott J. Miller,et al.  Bis(oxazoline) and Bis(oxazolinyl)pyridine Copper Complexes as Enantioselective Diels−Alder Catalysts: Reaction Scope and Synthetic Applications , 1999 .

[18]  M. Johannsen,et al.  Asymmetric hetero Diels-Alder reactions and ene reactions catalyzed by chiral copper(II) complexes , 1995 .

[19]  H. Kagan,et al.  Catalytic Asymmetric Diels-Alder Reactions , 1992 .

[20]  L. Szilágyi,et al.  Cycloaddition Reactions Leading to Carbohydrate Derivatives. Part II. Hetero Diels-Alder Reactions of Monosaccharide 1,1-Dithiooxalates and O-Thioformates. A Comparative Study , 1989 .

[21]  E. Vedejs,et al.  Generation of .alpha.-oxo dithioesters by dithiolanium ylide cycloreversion. Synthesis of 2-acyl-3,6-dihydro-2H-thiopyrans , 1980 .