Catalytic asymmetric addition of dialkylzinc reagents to alpha-aldiminoesters.
[reaction: see text] The first catalytic, enantioselective addition of organozinc reagents to alpha-aldiminoesters is described. The use of a Lewis acid/Lewis base containing bifunctional catalyst preorganizes both reactive substrates to promote enantioselective addition over the racemic background reaction and alternative addition modes. Alcohol additives were found to enhance the enantioselection. The addition product was also found to cyclize with remaining substrate to provide imidazolidines.
Basra
Sandeep
S
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, 19104, USA.
Fennie
Michael W
MW
Kozlowski
Marisa C
MC
D002384:Catalysis; D003500:Cyclization; D004952:Esters; D048289:Imidazolidines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D004952:Esters; D048289:Imidazolidines; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D015032:Zinc