A Chiral Primary Amine Thiourea Catalyst for the Highly Enantioselective Direct Conjugate Addition of α,α‐Disubstituted Aldehydes to Nitroalkenes

Mathieu P. Lalonde, Yonggang Chen, Eric N. Jacobsen

Angewandte Chemie International Edition · 2006 · 373 citations · 81 references

Concepts

Abstract

Dual activation: The bifunctional primary amine thiourea catalyst 1 promotes the highly enantioselective direct conjugate addition of α-branched aldehydes to nitroalkenes (see scheme). Cooperative activation of both the nucleophile and electrophile allows the use of mild reaction conditions and provides access to a wide variety of adducts with vicinal quaternary and tertiary stereogenic centers (>90 % ee).

References

81