146430-30-0Relevant academic research and scientific papers
A Novel Concept for Regiochemical and Stereochemical Control in Lewis Acid Promoted Annulation Reactions
Molander, Gary A.,Cameron, Kimberly O.
, p. 2617 - 2619 (1991)
Studies on the regioselective and stereoselective formation of a variety of 2-carbalkoxy-8-oxabicyclooctan-3-ones by means of a Lewis acid promoted annulation process leads to a novel concept for selectivity in Lewis acid promoted carbonyl
Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
Molander, Gary A.,Camera, Kimberly O.
, p. 830 - 846 (2007/10/02)
Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.
BIS(TRIMETHYLSILYL) ENOL AS 1,3-DIANON EQUIVALENTS: REGIOCONTROLLED AND ANNULATION REACTIONS
Molander, Gary A.,Andrews, Steven W.
, p. 2351 - 2354 (2007/10/02)
In the presence of titanium tetrachloride, 1,3-bis(trimethoxysiloxy)-1-methoxy-1,3-butadiene (1) undergoes facile annulation reactions with 1,4 -and 1,5-dielectrophiles to generate seven- and eight-membered bicyclic ether adducts.The annulations occur in good yields (49-83percent) and are also highly regioselective for substrates containing two distinct electrophilic groups.
