144686-29-3Relevant 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 (1992)
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.
A New Method for the Preparation of γ-Hydroxy Ketones: a Formal Total Synthesis of (+/-)-Lanceol
Fuji, Kaoru,Node, Manbu,Usami, Yoshihide,Kiryu, Yoshimitsu
, p. 449 - 450 (2007/10/02)
The reaction of methyl esters with 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide followed by treatment with silica gel affords γ-hydroxy ketones.
