135895-69-1Relevant academic research and scientific papers
A Selectivity Study of Activated Ketal Reduction with Borane Dimethyl Sulfide
Bartels, Birgit,Hunter, Roger
, p. 6756 - 6765 (2007/10/02)
A chemo- and regioselectivity study of the reagent combination BH3*SMe2/TMSOTf for ketal reduction has been undertaken.It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products.A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative.A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.
The First Solvent-directed Regioselective Ketal Reduction of Unsymmetrical Glycols
Hunter, Roger,Bartels, Birgit
, p. 2887 - 2888 (2007/10/02)
Borane-dimethyl sulphide/TMSOTf in THF reduces ketals of unsymmetrical vicinal diols with much higher regioselectivity than with CH2Cl2 as solvent.
