133885-13-9Relevant 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.
Reduction of activated ketals with borane-dimethyl sulphide
Hunter, Roger,Bartels, Birgit,Michael, Joseph P.
, p. 1095 - 1098 (2007/10/02)
Borane-Dimethyl sulphide reduces ketals activated with TMSOTf at -78°C in dichloromethane. The scope and selectivity of the reagent has been investigated.
