Monobenzylated isosorbide

The ene reaction of fuUerene (C o) with 3-methylene-2,3-dihydrofuran gives an easily isolated addition product in good yield <96JOC2559>. There is a continuous need for chiral acrylate esters for asymmetric Diels-Alder reactions with high diastereoselectivity. Lewis acid promoted Diels-Alder reactions of acrylate esters from monobenzylated isosorbide 28 (or isomannide) and cyclopentadiene provided exclusively e db-adducts with good yields and high diastereoselectivity <96TL7023>. 

The reaction of monobenzylated isosorbide D with ditosylates (Eq. 35) is more subtle the microwave-specific effect (Tab. 3.15) appeared when the temperature was lowered to 80 °C (modulated by the presence of cyclohexane) whereas it was masked by a higher temperature of 110 °C (maintained by the use of toluene) [89]. 

Tab. 3.15 Yield (% E) from reaction of monobenzylated isosorbide (D) with ditosylates for 15 min.

Loupy, A, Monteux, D, Asymmetric Diels-Alder monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries. Tetrahedron Lett., 37, 7023-7026, 1996. 

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See also in sourсe #XX -- [ ]

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