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

Hofmayer, Maximilian S.; Sunagatullina, Alisa; Broesamlen, Daniel; Mauker, Philipp and Knochel, Paul (2020): Stereoselective Cobalt-Catalyzed Cross-Coupling Reactions of Arylzinc Chlorides with alpha-Bromolactones and Related Derivatives. In: Organic Letters, Vol. 22, No. 4: pp. 1286-1289

Abstract

alpha-Bromolactones bearing a substituent in the beta-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 degrees C, 16 h) leading to optically enriched alpha-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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English