Highly Enantioselective Addition of 1‐Fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐Unsaturated Aldehydes

Martin Kamlar, Natalia Bravo, Andrea‐Nekane R. Alba, Simona Hybelbauerová, Ivana Cı́sařová, Ján Veselý, Albert Moyano, Ramón Rios

European Journal of Organic Chemistry · 2010 · 31 citations · 38 references

Concepts

Abstract

Abstract An organocatalytic, highly enantioselective addition of 1‐fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X‐ray diffraction analysis.

References

38