Elegant Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentanes

Abstract

The conversion of cyclic Baylis–Hillman acetates 1 into the corresponding cyano derivatives 2 was achieved using potassium cyanide in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in aqueous medium. The obtained Michael acceptors 2 easily add primary amines in absolute ethanol to produce a new family of 1,2,3-trisubstituted cyclpentanes 3 in good yields.

GRAPHICAL ABSTRACT

Keywords:

• Baylis–Hillman acetates
• DABCO
• primary amines
• 1,2,3-trisubstituted cyclopentanes

Notes

^a Isolated yield after chromatography.

^a Isolated yield after chromatography.