Products Cited in Publications Worldwide Charge‐activated TADDOLs: Recyclable organocatalysts for asymmetric (hetero‐) Diels–Alder reactions

Charge‐activated TADDOLs: Recyclable organocatalysts for asymmetric (hetero‐) Diels–Alder reactions

George F. Riegel; Keiji Takashige; Alex Lovstedt; Steven R. Kass

DOI:

Abstract

Several charge-containing TADDOL salts were synthesized and used as organocatalysts in asymmetric Diels–Alder and hetero-Diels–Alder reactions. Their catalytic activity was found to exceed that of a noncharged analog while maintaining or improving upon the enantioselectivity. The enhanced activities of the TADDOL salts enabled them to act as presumed hydrogen bond donor catalysts in the Diels–Alder and hetero-Diels–Alder reactions of 1,3-cyclohexadiene with methyl vinyl ketone at 40°C and 2-phenoxy-1,3-butadiene with ethyl glyoxylate at room temperature, respectively. Given the ionic nature of these charge-activated catalysts, it also proved possible to recycle and reuse the TADDOL without chromatography or the need for a recrystallization.

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