TADDOL‐Based Phosphane–Phosphite Ligands in Enantioselective Cu‐Catalyzed Grignard 1,4‐Additions Followed by Mannich‐Type Alkylations

Michal Drusan, Wibke Lölsberg, Andrea Škvorcová, Hans‐Günther Schmalz, Radovan Šebesta

European Journal of Organic Chemistry · 2012 · 18 citations · 34 references

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Abstract

Abstract Copper(I) complexes of TADDOL‐based phosphane–phosphite ligands catalyze enantioselective conjugate additions of various Grignard reagents to cyclic enones. Through trapping of the resulting chiral magnesium enolates with N ‐benzylidene‐4‐methylbenzenesulfonamide (as an imine) in one‐pot procedures, the corresponding Mannich products (i.e., β‐aminocarbonyl compounds) were obtained in good yields and high enantiomeric purities, although with only low diastereoselectivities.

References

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