ASYMMETRIZED TRIS (HYDROXYMETHYL)METHANE AS A HIGHLY STEREODIVERGENT CHIRAL BUILDING BLOCK: PREPARATION OF ALL FOUR STEREOISOMERS OF PROTECTED 2-HYDROXYMETHYL-1,3-BUTANEDIOL

Article abstract of DOI:10.1016/S0040-4039(00)97081-3

Monoacetate 3 is a synthetic equivalent of asymmetrized tris(hydroxymethyl)methane 1, which is a new chiral building block endowed with latent C_3v symmetry.Thanks to this property, starting from a single enantiomer 3, it is possible to get not only both (R) and (S) aldehydes 7, but also all the stereoisomers deriving from addition of a C-nucleophile to 7, just relying on a single diastereocontrol (double stereodivergency).