Tetrahedron Letters p. 2095 - 2098 (1992)
Update date:2022-08-03
Topics: Functionalization Deprotection Isolation and Purification Asymmetric Dihydroxylation
Oi, Ryu
Sharpless, K. Barry
Asymmetric dihydroxylation (ADH) of acrolein acetals afforded optically active glyceraldehyde equivalents. Enantiopure 3-(1,2-dihydroxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine 3, a protected glyceraldehyde, was obtained from the corresponding acrolein acetal 2 by ADH and subsequent recrystallization. Enantiopure 3-(1,2-epoxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine 5, a protected glycidaldehyde, was produced in two steps from 3.
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