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Synfacts 2015; 11(1): 0067
DOI: 10.1055/s-0034-1379755
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

(–)-Sparteine versus (+)-Sparteine Surrogates in Copper(II)–Diamine-Catalyzed Reactions

Contributor(s):
Hisashi Yamamoto
,
Wafa Gati
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
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Publication History

Publication Date:
15 December 2014 (online)

 
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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.


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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.


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