Tetrahedron Letters p. 937 - 938 (1995)
Update date:2022-07-29
Topics:
Saimoto, Hiroyuki
Yatani, Setsuo
Sashiwa, Hitoshi
Shigemasa, Yoshihiro
Although aldol condensation of 1,3-dihydroxyacetone with formaldehyde in methanol catalyzed by CaCl2/KOH gave glycero-tetrulose, the reaction catalyzed by Ca(OH)2 preferentially gave 1,3-dihydroxyacetone dimer. The result was explained by the formation of a chelated enolate. This sequence was successfully applied to the stereoselective synthesis of threo-3-pentulose.
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