Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates.
Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α-amino phosphonate into its authentic N-Cbz derivative.
Kaur
Parminder
P
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
Wever
Walter
W
Rajale
Trideep
T
Li
Guigen
G
D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry; D013237:Stereoisomerism
D007097:Imines; D063065:Organophosphonates; D017905:Phosphites; D008094:Lithium