CHIRAL α-METHOXY-E-CROTYLBORONATES, REAGENTS FOR STEREOSELECTIVE C-C-BOND FORMATION UNDER REAGENT CONTROL OF DIASTEREOSELECTIVITY

Article abstract of DOI:10.1016/S0040-4039(00)96714-5

Treatment of the previously described α-chloro-E-crotylboronate with lithium-methoxide in THF furnished the title compound 6 of 88-94 percent e.e.On addition to achiral aldehydes complete transfer of chirality was realized, resulting in the β-methyl-homoallyl alcohols 7 with a Z-configuration of the enol-ether double bond.On reaction of 6 with chiral aldehydes excellent (matched pair) to good (mismatched pair) selectivities in favor of the stereotriades C or D respectively were realized.