Sequential Mukaiyama-Michael reaction induced by carbon acids.

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• The Mukaiyama-Michael reaction is a crucial carbon-carbon bond-forming reaction.
• Sequential reactions offer efficient pathways to complex molecules.

Purpose of the Study:

• To develop a sequential Mukaiyama-Michael reaction utilizing two different Michael acceptors.
• To synthesize novel cyclic ketene silyl acetals.

Main Methods:

• Employing a strong carbon acid catalyst.
• Utilizing ketene silyl acetal derived from ethyl acetate (EtOAc).
• Reacting with α-pyrones as primary acceptors followed by secondary acceptors.

Main Results:

• Successful execution of the sequential Mukaiyama-Michael reaction.
• Formation of reactive cyclic ketene silyl acetals.
• Demonstrated reactivity of the cyclic ketene silyl acetals with subsequent acceptors.

Conclusions:

• The developed sequential reaction is effective for synthesizing functionalized cyclic ketene silyl acetals.
• The intermediate cyclic ketene silyl acetals are versatile synthons for further elaboration.