Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes: a catalytic route to beta2-amino acids, aldehydes, and alcohols.
Using chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition to acyclic nitroalkenes for the first time, we obtained enantioselectivities up to 98%. The use of acyclic substrates with different dialkylzinc reagents provides a catalytic enantioselective route to (functionalized) beta2-amino aldehydes, acids, and alcohols.
Duursma
Ate
A
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, The Netherlands.
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000080:Acetals / Q000737:chemistry; D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D009574:Nitro Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000080:Acetals; D000438:Alcohols; D000447:Aldehydes; D000475:Alkenes; D000596:Amino Acids; D009574:Nitro Compounds; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D015032:Zinc; C454811:diethylzinc