Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones.
The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Thomson
Regan J
RJ
D000478:Alkylation; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D008958:Models, Molecular; D009281:Naphthalenes / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*; D013871:Thiones / Q000737:chemistry*
C406943:BINAP, 2-naphthol; D004952:Esters; D009281:Naphthalenes; D009942:Organometallic Compounds; D013844:Thiazoles; D013871:Thiones; D009532:Nickel