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s D-mannitol ref. 1 O O N O Bn O O BnNHOH CH2Cl2, MgSO4 r.t., 2 h, 95% 1 O (A) The SmI2-mediated reaction of nitrone 1 with ethyl or methyl acrylate led in fairly good yields to the expected g-N-hydroxyamino esters;3 in both cases, the anti configuration was preferred. The anticonfigured methyl ester product is a known intermediate in the synthesis of (S)-vigabatrin.3,4 (B) Allylzinc bromide regioselectively added to 1 in very good yield,5 whereby homoallylic hydroxylamines were observed with different stereoselectivities depending on the presence or the absence of Et2AlCl. A slightly higher diastereofacial anti-selectivity was observed with allylzinc bromide than with the previously reported allylmagnesium chloride.6 (C) The Mannich-type reaction of nitrone 1 and 2-silyloxy silyl ketene acetal 2 was performed with high stereocontrol to give the resulting adducts in good yields.7 When the addition was performed in the presence of Zn(OTf)2, the (2S,3S,4S)-configured product was formed as single isomer, whereas the use of SnCl4 led to the (2R,3R,4S)-configured isomer with high preference. COOR O O COOR N HO Bn

N-Benzyl-2,3-O-isopropylidene-d-glyceraldehyde Nitrone