1290544-13-6Relevant academic research and scientific papers
Indium-mediated allenylation of aldehydes and its application in carbohydrate chemistry: Efficient synthesis of D -ribulose and 1-deoxy- D -ribulose
Fischer, Michael,Schmoelzer, Christoph,Nowikow, Christina,Schmid, Walther
supporting information; experimental part, p. 1645 - 1651 (2011/05/05)
A two-step reaction sequence starting with the indium-mediated allenylation of aldehydes with 4-bromo-2-butyn-1-ols and subsequent ozonolysis of the resulting allenylic product was developed to generate a variety of dihydroxyacetone derivatives. The regioselectivity of the indium-promoted C-C bond-forming reaction can be manipulated through hydroxy protecting groups on 4-bromo-2-butyn-1-ol, yielding either allenes or alkynes as preferred products. Compared to established protocols, the necessary amount of indium for this type of allenylation can be decreased by a factor of two to four. The versatility of this strategy was demonstrated in thestereoselective and straightforward synthesis of D-ribulose and 1-deoxy-D-ribulose. Copyright
