Canipa SJ, Stute A, O’Brien P * University of York, Heslington, UK
Use of Copper(II)/Diamine Catalysts in the Desymmetrisation of
meso-Diols and Asymmetric Henry Reactions: Comparison of (‒)-Sparteine and (+)-Sparteine
Surrogates.
Tetrahedron 2014;
70: 7395-7403
Key words
asymmetric desymmetrization - Henry reaction - diamines - copper
Significance
O’Brien and co-workers present an evaluation of copper(II)–diamine complexes comprising
(–)-sparteine, (+)-sparteine surrogates, and Alexakis diamine in the desymmetrization
of meso-diols and asymmetric Henry reaction. One of the nitro alcohol products was utilized
in a concise synthesis of a chiral morpholine.
Comment
In order to compare the reactivity in asymmetric induction, the copper(II)–diamine
catalysts, containing diamine 1 and 2, were investigated in the enantioselective monobenzoylation of meso-1,2-diols and in the asymmetric Henry reaction. In both reactions the products were
obtained in good to high enantioselectivities with the opposite sense of induction
depending on the used diamine. As expected, (+)-sparteine surrogate 2 generated the antipodal products of those obtained using (–)-sparteine.
