ol9b04564_si_001.pdf (9.94 MB)

Stereoselective Cobalt-Catalyzed Cross-Coupling Reactions of Arylzinc Chlorides with α‑Bromolactones and Related Derivatives

Download (9.94 MB)
journal contribution
posted on 30.01.2020, 14:35 by Maximilian S. Hofmayer, Alisa Sunagatullina, Daniel Brösamlen, Philipp Mauker, Paul Knochel
α-Bromolactones bearing a substituent in the β-position undergo a highly trans-diastereoselective arylation with arylzinc chlorides in the presence of 10–20% CoCl2 and 10–20% PPh3 in THF under mild conditions (25 °C, 16 h) leading to optically enriched α-arylated lactones and protected aldol products (99% ee) in 52–96% yield. The synthetic utility of this arylation was demonstrated by the stereoselective preparation of an artificial rotenoid MOM-protected munduserol derivative.