18407-42-6Relevant articles and documents
A highly diastereomerically enriched, silyl-substituted alkyl lithium, configurationally stable at room temperature
Strohmann, Carsten,Abele, Bors C.,Lehmen, Klaus,Schildbach, Daniel
, p. 3136 - 3139 (2007/10/03)
The opening or blocking of a coordination site at the lithium center (for example by attachment of THF, see picture; left) leads to diastereodivergent courses in the reactions of a highly diastereomerically enriched alkyl lithium with Me3SnCl. At room temperature in noncoordinating solvents the reagent is configurationally stable and epimerizes in the presence of THF. (Chemical Equation Presented)
Vinyl Anion Equivalent V. Asymmetric Synthesis of Allylic Alcohols Using Chiral 2-(Trialkylsilyl)ethyl Sulfoxides
Kusuda, Shinya,Ueno, Yoshio,Toru, Takeshi
, p. 1045 - 1062 (2007/10/02)
Both enantiomers of optically pure secondary allylic alcohols can be conveniently prepared by the diastereoselective reaction of the α-sulfinyl carbanion of p-tolyl 2-(trialkylsilyl)ethyl sulfoxides or tert-butyl 2-(trimethylsilyl)ethyl sulfoxide with aldehydes followed by either fluoride-induced desilylsulfinylation or thermal elimination of the sulfinyl group.