The High-Pressure [4+2] Cycloaddition of Activated 1,3-Dienes to Nonactivated­ Heterodienophiles Derived from Glycolaldehyde

Abstract

[4+2] Cycloaddition of 1,3-dienes to glycolaldehyde derivatives, leading to 5,6-dihydro-2H-pyrans, was effected by high pressure (10 kbar) in the presence of Eu(fod)₃ (2%). Enantioselective version of the reaction was also studied.

aldehydes - asymmetric catalysis - Diels-Alder reaction - Lewis acids - stereoselectivity

References

<A NAME="RP05102SS-1">1</A> Butlerov A. Liebigs Ann. Chem.  1861,  120:  295 

<A NAME="RP05102SS-2">2</A> Hanessian S. Preparative Carbohydrate Chemistry   Marcel Dekker; New York: 1997. 

<A NAME="RP05102SS-3">3</A> David S. Eustache J. Lubineau A. J. Chem. Soc., Perkin Trans. 1  1974,  295 

<A NAME="RP05102SS-4">4</A> Konowal A. Jurczak J. Zamojski A. Rocz. Chem.  1968,  42:  2045 ; Chem. Abstr. 1969, 71, 3209

<A NAME="RP05102SS-5">5</A> Zamojski A. Banaszek A. Grynkiewicz G. Adv. Carbohydr. Chem. Biochem.  1982,  40:  1 

<A NAME="RP05102SS-6">6</A> Jørgensen KA. Angew. Chem. Int. Ed.  2000,  39:  3558 ; and references cited therein

<A NAME="RP05102SS-7">7</A> Jurczak J. Chmielewski M. Filipek S. Synthesis  1979,  41 

<A NAME="RP05102SS-8">8</A> Jurczak J. Pikul S. Bauer T. Tetrahedron  1986,  42:  447 

<A NAME="RP05102SS-9">9</A> Jurczak J. Golebiowski A. Chem. Rev.  1989,  89:  149 

<A NAME="RP05102SS-10">10</A> Bednarski M. Danishefsky S. J. Am. Chem. Soc.  1983,  105:  3716 

<A NAME="RP05102SS-11">11</A> Jurczak J. Golebiowski A. Bauer T. Synthesis  1985,  928 

<A NAME="RP05102SS-12">12</A> Golebiowski A. Jacobsson U. Jurczak J. Tetrahedron  1987,  43:  3063 

<A NAME="RP05102SS-13">13</A> Schaus SE. Branalt J. Jacobsen EN. J. Org. Chem.  1998,  63:  403