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Synfacts 2008(9): 0950-0950  
DOI: 10.1055/s-2008-1078638
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Sc(III)-Catalyzed Direct Allylation of Aldimines

Contributor(s):Mark Lautens, Valentina Aureggi
X. Li, X. Liu, Y. Fu, L. Wang, L. Zhou, X. Feng*
Sichuan University, Chengdu, P. R. of China
Direct Allylation of Aldimines Catalyzed by C 2-Symmetric N,N′-Dioxide-ScIII Complexes: Highly Enantioselective Synthesis of Homoallylic Amines
Chem. Eur. J.  2008,  14:  4796-4798  
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Publication History

Publication Date:
22 August 2008 (online)

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Key words

aldimines - allylation - amines

Significance

The efficient catalytic asymmetric three-component allylation of aldimines is reported. The resulting optically active homoallylic amines are versatile intermediates in the organic synthesis and are obtained in high yield with excellent enantioselectivity under mild conditions. This paper builds on previous work in the field pioneered by Mosset, Wips, and Kobayashi (e.g., see: B. Choucair, H. Léon, M.-A. Miré, C. Lebreton, P. Mosset Org. Lett. 2000, 2, 1851).

Comment

The authors have previously reported the application of N,N′-dioxide metal complexes in catalytic asymmetric reactions (J. Org. Chem. 2008, 73, 630). Herein, the direct asymmetric ­allylation of aldimines is promoted by a selected C 2-symmetric N,N′-dioxide-Sc(III) complex. The ligand is easily synthesized from the corresponding readily available chiral amino acid and amine. The scope includes a variety of aromatic aldehydes. Substituents on the aromatic ring do not affect the enantioselectivity of the reaction (up to 97% ee). Heteroaromatic aldehydes are also suitable substrates for this transformation and the corresponding products are obtained in good yields and enantioselectivities (71-81% yield, 87-96% ee)

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