Tetrahedron Letters p. 969 - 972 (1994)
Update date:2022-08-04
Topics:
Lillie
Avery
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.
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