A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides.
Substituted succinic and glutaric anhydrides undergo a nickel-catalyzed monofunctionalization with organozinc reagents as nucleophiles. The reaction proceeds readily with a variety of substrates, employs commercially available or readily attainable reagents, tolerates sensitive functionality on both partners, and affords the product ketoacids in moderate to high yields. The use of a chiral phosphinooxazoline results in a desymmetrization of a meso anhydride to provide the ketoacid in 85% yield and 79% ee.
Bercot
Eric A
EA
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Rovis
Tomislav
T