Asymmetric Aza-Henry Reactions from N-p-Tolylsulfinylimines
- Resource Type
- Authors
- José L. García Ruano; M. Belén Cid; José Alemán; Modesto J. Remuinan; Markus Topp; Jesús López-Cantarero
- Source
- Organic Letters. 7:4407-4410
- Subject
- Reaction rate
chemistry.chemical_classification
chemistry.chemical_compound
Aldimine
Nitromethane
chemistry
Organic Chemistry
Organic chemistry
Stereoselectivity
General Medicine
Physical and Theoretical Chemistry
Biochemistry
Medicinal chemistry
- Language
- ISSN
- 1523-7052
1523-7060
[reaction: see text] N-Sulfinylimines derived from aromatic or aliphatic aldehydes and ketones react with nitromethane and NaOH in a highly diastereoselective manner under mild conditions. In the presence of TBAF, the reaction rates are strongly increased and the stereoselectivity is inverted. This method provides enantiomerically pure beta-nitroamines derived from enolizable aldimines and ketimines, which so far are hardly accessible by aza-Henry reactions.