Effect of Increase in Steric Bulk of Aryllithium on Stereoselectivity of Boronate Complexes
Corresponding Author(s) : Habib Hussain
Asian Journal of Chemistry,
Vol. 25 No. 17 (2013): Vol 25 Issue 17 page 9965-9969
(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 ºC and room temperature. It was observed that the increase in steric bulk of aryl lithium (ArLi) resulted in the lower yields and enantiomeric ratios.
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