Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)

Article abstract of DOI:10.1016/S0040-4039(00)73941-4

The asymmetric synthesis of epimeric α-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotylbutyltin to asymmetrized bis(hydroxymethyl) acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both anantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.