A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines

Cinchona alkaloid-derived thiourea catalysts promote nucleophilic additions to acyl imines for the asymmetric synthesis of secondary amine adducts. The hydroquinine-derived thiourea catalyst efficiently promotes the aza-Henry reaction of nitroalkane with acyl imines, affording β-nitroamines in good...

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Bibliographic Details
Published in:Tetrahedron 2006-12, Vol.62 (49), p.11499-11505
Main Authors: Bode, Christiane M., Ting, Amal, Schaus, Scott E.
Format: Article
Language:English
Subjects:
Aza-Henry reaction
Cinchona alkaloids
Imines
Mannich reaction
Organic catalysis
Thiourea
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Summary:Cinchona alkaloid-derived thiourea catalysts promote nucleophilic additions to acyl imines for the asymmetric synthesis of secondary amine adducts. The hydroquinine-derived thiourea catalyst efficiently promotes the aza-Henry reaction of nitroalkane with acyl imines, affording β-nitroamines in good yields with enantioselectivities of 90–98% ee and diastereoselectivities up to 97%. The scope of the reaction also includes dimethyl malonate as a nucleophile to access β-amino esters in high enantiopurity. Under the optimized reaction conditions, secondary amine adducts of high enantiopurity are generated based on various aromatic and α,β-unsaturated acyl imines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.07.071