The protection of ketones and aldehydes as 4-trimethylsilylmethyl-1,3- dioxolanes

Article abstract of DOI:10.1016/S0040-4039(00)79941-2

The 1,3-dioxolanation of carbonyl compounds with 2,3- bis(trimethylsilyloxy)-trimethylsilylpropane (BTTP) in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf) has been investigated. BTTP readily converted unhindered ketones and aldehydes to their corresponding 4-trimethylsilylmethyl-1,3-dioxolanes, but failed for more hindered substrates. The 4-trimethylsilylmethyl-1,3-dioxolane can be selectively cleaved to regenerate the carbonyl compound in the presence of a 1,3-dioxolane using either LiBF₄ or HF in acetonitrile.