Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl) acetaldehydes (BHYMA)

Article abstract of DOI:10.1016/0040-4039(91)80449-G

MgBr₂ catalysed allylation of a series of diprotected asymmetrized bis (Hydroxymethyl) acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH₂OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.