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Highly Diastereo- and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts

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  • This work was supported by a Grant-in-Aid for Scientific Research from MEXT (Japan).

Abstract

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High selectivity: A highly diastereo- and enantioselective Mannich reaction between a synthetically flexible ketimine and aldehydes has been developed. The syn- or anti-Mannich products contain tetrasubstituted chiral carbon centers and were obtained with almost complete stereoselectivity by using either L-proline or an axially chiral aminosulfonamide, respectively, as the catalyst (see scheme, Tf=trifluoromethanesulfonyl).

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