Diethyl (cyanofluoromethyl)phosphonate: Application in catalytic enantioselective Michael additions

GRAPHICAL ABSTRACT

ABSTRACT

Three types of chiral catalysts: a chincona-based squaramide, TADDOL and a group of sugar-based crown ethers were applied to the asymmetric Michael addition of diethyl (cyanofluoromethyl)phosphonate to diverse Michael acceptors. Two of the crown ether catalysts resulted in high yields and enantioselectivities with trans-β-nitostyrene as in case of the chincona-based squaramide catalyst the yield was low with high enantioselectivity. TADDOL proved to be active, but less selective in the Michael addition.

KEYWORDS:

• Fluorophosphonates
• catalytic enantioselective Michael additions
• sugar-based crown ethers

Acknowledgment

We thank Dr. Tibor Soós for the catalyst 3.

Funding

This work was financially supported by the Hungarian Scientific Research Found (OTKA Grant Nos. PD 112166 and K 108752).