1338073-53-2Relevant academic research and scientific papers
Effect of increase in steric bulk of aryllithium on stereoselectivity of boronate complexes
Hussain, Habib,Gilani, Syeda Rubina,Ali, Zulfiqar,Hussain, Imdad
, p. 9965 - 9969 (2014/01/06)
(S)-4,4,5,5-Tetramethyl-2-(4-phenylbutan-2-yl)-1,3,2-dioxaborolane was reacted with 1-bromonaphthalene and ate-complex was synthesized and this resulted product acted as nucleophile. Stereoselectivity of ate-complex was determined by reacting with different electrophiles diisopropyl azodicarboxylate (DIAD), dibenzyl azodicarboxylate (DBAD) and tropylium tetrafluoroborate. Yields and enantiomeric ratios (e.r.) were measured at -78 °C and room temperature. It was observed that the increase in steric bulk of aryl lithium (ArLi) resulted in the lower yields and enantiomeric ratios.
Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis
Larouche-Gauthier, Robin,Elford, Tim G.,Aggarwal, Varinder K.
supporting information; experimental part, p. 16794 - 16797 (2011/12/04)
The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the arsenal of methods for use in asymmetric organic synthesis.
