116332-80-0Relevant academic research and scientific papers
201. Reactions of Chiral 2-(tert-Butyl)-2H,4H-1,3-dioxin-4-ones Bearing Functional Groups in the 6-Position and Diastereoselective Catalytic Hydrogenation to cis-2,6-Disubstituted 1,3-Dioxan-4-ones
Noda, Yoshihiro,Seebach, Dieter
, p. 2137 - 2145 (1987)
(R)-5-Bromo-6-(bromomethyl)-2-(tert-butyl)-2H,4H-1,3-dioxin-4-one (2) derived from (R)-3-hydroxybutanoic acid used for substitutions and chain elongations at the side-chain C-atom in the 6-position of the heterocycle (->3-6, 10-13).Subsequent simultaneous reductive debromination and double-bond hydrogenation (Pd/C, H2) occurs with essentially complete diastereoselectivity (>98percent ds), with H transfer from the face opposite to the t-Bu group (->15-20, Table 1).Hydrolytic cleavages of the dioxanones then lead to enantiomerically pure β-hydroxy-acid derivatives (overall self-reproduction of the stereogenic center of 3-hydroxybutanoic acid or alkylation in the 4-position of this acid with preservation of configuration).
Diastereoselective synthesis of polypropionates: Cationic couplings of 4-acetoxy-1,3-dioxanes with crotyl-metal reagents
Rychnovsky, Scott D.,Sinz, Christopher J.
, p. 6811 - 6814 (2007/10/03)
Lewis acids promote the coupling of 4-acetoxy-1,3-dioxanes 1 with crotyl-metal species to generate propionate motifs such as 2. The reactions show a marked dependence on Lewis acid, the crotyl metal species, and the presence and stereochemical disposition of a C5 methyl group. A 1,3-syn methyl relationship is favored in these additions.
