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Paper | Special issue | Vol 97, No. 2, 2018, pp.744-754
Published online, 26th April, 2018
DOI: 10.3987/COM-18-S(T)43
Palladium-Catalyzed Asymmetric Haloiminolactonization of α-Allylmalonamides

Masami Kuriyama, Kosuke Yamamoto, Keiko Ishimaru, Noriyuki Fujimura, Daishiro Minato, and Osamu Onomura*

*Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

A catalyst composed of 10 mol% of Pd(OAc)2 and (R,R)-PhBox was proven to be effective in the asymmetric haloiminolactonization of α-allylmalonamides with N-halosuccinimides, giving the dihalogenated cyclic products with good diastereomeric ratio (up to 89/11) and enantiomeric excess (up to 72% ee).