A facile and efficient anti-selective four-component direct aldol addition via chemoselective thioester enolate formation.
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.
Zhou
Guoqiang
G
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Yost
Julianne M
JM
Sauer
Scott J
SJ
Coltart
Don M
DM