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Solution Structures of the Mixed Aggregates Derived From Lithium Acetylides and a Camphor-Derived Amino Alkoxide

Solution Structures of the Mixed Aggregates Derived From Lithium Acetylides and a Camphor-Derived Amino Alkoxide

T F Briggs, M D Winemiller, B Xiang, D B Collum

J Org Chem. 2001 Sep 21;66(19):6291-8.

PMID: 11559177

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4440011	Lithium phenylacetylide solution		4440-01-1	Price

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