Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et2AlCN using amino alcohols and BINOLs as catalysts.
The asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines with Et(2)AlCN has been established. Both free amino alcohols and BINOLs have been proven to be effective catalysts to afford excellent enantioselectivities and yields. The N-phosphonyl group can be readily cleaved under mild conditions and enable purification of crude products by simple washing with hexane. The cleaved N,N-dialkyl diamine auxiliary can be recovered quantitatively via n-BuOH extraction. The scope for both N-phosphonyl imines and catalysts was vastly studied for this new catalytic system.
Kaur
Parminder
P
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
Pindi
Suresh
S
Wever
Walter
W
Rajale
Trideep
T
Li
Guigen
G
D000535:Aluminum / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; C406944:BINOL, naphthol; D007097:Imines; D009284:Naphthols; D009942:Organometallic Compounds; D000535:Aluminum