503473-27-6Relevant articles and documents
Asymmetric synthesis of (S,S)- and (R,R)-2-methylthreitol
Enders, Dieter,Peiffer, Evelyn,Raabe, Gerhard
, p. 1021 - 1026 (2008/02/02)
The asymmetric synthesis of (S,S)- and (R,R)-2-methylthreitol was carried out, starting from the SAMP or RAMP hydrazone of 2,2-dimethyl-1,3-dioxan-5-one. The protocol involves an enantioselective α-alkylation as a key step. The second stereogenic center was installed by either nucleophilic 1,2-addition or diastereoselective epoxidation with bis(acetylacetonato)oxovanadium(IV) [VO(acac)2] as catalyst. The title compounds were obtained in excellent diastereo- and enantiomeric excesses (≥98% de, 98% ee) and in good overall yields (40-61%). Georg Thieme Verlag Stuttgart.