Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane.
[reaction: see text] The first organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane has been realized by using cupreine (2) or 9-O-benzylcupreine (3) as the catalyst. Both catalysts are highly reactive and highly enantioselective. alpha-Hydroxy-beta-nitrophosphonates have been synthesized in good yields and excellent enantioselectivities (>or=90% ee) at a low catalyst loading (5 mol %). These nitroaldol products may be reduced to the biologically significant beta-amino-alpha-hydroxyphosphonates with complete retention of the stereochemistry.
Mandal
Tanmay
T
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
Samanta
Sampak
S
Zhao
Cong-Gui
CG
D002384:Catalysis; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D009595:Nitroparaffins / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism
D009595:Nitroparaffins; D010758:Phosphorus; D009584:Nitrogen; D008697:Methane; C008640:nitromethane