144686-27-1Relevant academic research and scientific papers
2,2-Dimethyl-1,3-oxathiane 3,3-dioxide: A γ-hydroxypropyl anion equivalent
Fuji,Usami,Kiryu,Node
, p. 852 - 858 (2007/10/02)
The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2,2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.
THE REACTION OF 2,2-DIMETHYL-4-LITHIO-1,3-OXATHIANE 3,3-DIOXIDE. GENERAL SYNTHESIS OF γ-HYDROXYKETONES
Fuji, Kaoru,Node, Manabu,Usami, Yoshihide
, p. 961 - 962 (2007/10/02)
Reaction of 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide ( 2 ) with alkyl halides and carbonyl compounds proceed smoothly to give 4-substituted heterocycles.A general synthesis of γ-hydroxyketones from aldehydes utilizing 2 is described.
