A Facile and Efficient Anti-Selective Four-Component Direct Aldol Addition via Chemoselective Thioester Enolate Formation
Organic Letters2007Vol. 9(22), pp. 4663–4665
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Abstract
A facile and efficient four-component anti-selective direct aldol addition of thioester enolates has been developed that is fully compatible with enolizable aldehydes and able to be conducted using untreated reagent-grade CH2Cl2 open to the air. The thioester enolates are generated in situ via an acylation/conjugate addition sequence using commercially available PhSLi and acryloyl chloride, thus avoiding prior enolate formation while maintaining complete chemoselectivity. The organosulfur products are convertible into various polyketide-based structures.
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