Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution.

Autor: Kam, Mei Kee, Sugiyama, Akira, Kawanishi, Ryouta, Shibatomi, Kazutaka
Předmět:
Zdroj: Molecules; Sep2020, Vol. 25 Issue 17, p3902-3902, 1p
Abstrakt: Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index