%0 Journal Article
%A Briggs, Timothy F.
%A Winemiller, Mark D.
%A Xiang, Bosong
%A Collum, David B.
%D 2001
%T Solution Structures of the Mixed Aggregates Derived from
Lithium Acetylides and a Camphor-Derived Amino Alkoxide
%U https://acs.figshare.com/articles/journal_contribution/Solution_Structures_of_the_Mixed_Aggregates_Derived_from_Lithium_Acetylides_and_a_Camphor-Derived_Amino_Alkoxide/3689406
%R 10.1021/jo010305b.s001
%2 https://ndownloader.figshare.com/files/5779758
%K C 2
%K solution Structures
%K PhCCLi
%K THF
%K Mixed Aggregates Derived
%K trifluoromethyl ketone
%K RCCLi
%K lithium cyclopropylacetylide
%K 15 N NMR spectroscopies
%K lithium phenylacetylide
%K 13 C
%K stoichiometrie
%K Lithium Acetylides
%K tetramer
%X Low-temperature 6Li, 13C, and 15N 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 C2-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.
%I ACS Publications