Organic & Biomolecular Chemistry 1997-07-22

Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives.

C Y Shiau, M F Byford, R T Aplin, J E Baldwin, C J Schofield

Index: Org. Biomol. Chem. 10(30) , 6201-10, (2012)

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Abstract

A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.