Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents

作者：Yu Luo Ting; Ho Meng Tsung; Chang Ching Yao; Yang Teng Kuei^*

来源：Tetrahedron: Asymmetry , 2007, 18(8): 949-962.

DOI：10.1016/j.tetasy.2007.03.015

The Ni(acac)(2) catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of chiral alpha-bromopropionyl-2-oxazolidinones 2 with diethyl zinc under the catalysis of Ni(acac)(2), performed the asymmetric zinc-Reformatsky reaction with activated alpha-haloacetophenones 3 to give the chiral beta-hydroxyamide 4 in good yields and high ratios of syn-(2R,3R)-isomers (up to > 97%). This new asymmetric synthesis technology affords a practical method to synthesize the versatile chiral building block 5 for triazole antifungal agents, such as Voriconazole, Ravuconazole, TAK-187, and RO-0094815.

• 出版日期2007-5-16
• 单位四川大学