Solution Structures of the Mixed Aggregates Derived from Lithium Acetylides and a Camphor-Derived Amino Alkoxide
The Journal of Organic Chemistry2001Vol. 66(19), pp. 6291–6298
Citations Over TimeTop 20% of 2001 papers
Abstract
Low-temperature (6)Li, (13)C, and (15)N NMR spectroscopies reveal that mixtures of lithium cyclopropylacetylide or lithium phenylacetylide (RCCLi) and a vicinal amino alkoxide derived from camphor (R*OLi) in THF/pentane afford an asymmetric (RCCLi)(3)(R*OLi) mixed tetramer and a C(2)-symmetric (RCCLi)(2)(R*OLi)(2) mixed tetramer depending on the stoichiometries. The corresponding (RCCLi)(R*OLi)(3) mixed tetramer is not observed. R*OLi-mediated additions of PhCCLi to benzaldehyde proceed with up to an 8:1 enantiomeric ratio that depend on both the choice of R*OLi and the PhCCLi/R*OLi stoichiometries. The results are considered in light of a previously proposed mechanism for the 1,2-addition to a trifluoromethyl ketone.
Related Papers
- → Influence of SolGel processing on the morphology and crystallization of Mg2TiO4 powders(1989)3 cited
- Extracting Camphor and Camphor Oil from Camphor Trees(2000)
- Determination of Camphor in Dongchuang Ointment by GC(2008)
- Determination of camphor in camphor cream by UV spectrophotometry(2004)
- Determination of camphor in compound camphor spirit by high-performance liquid chromatography(2013)