This article is cited in 8 papers

Communications

Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols

S. G. Zlotin^a, O. A. Banina^b, D. V. Sudarikov^b, A. G. Nigmatov^a, L. L. Frolova^b, A. V. Kutchin<sup>b

a</sup> N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b Institute of Chemistry, Komi Science Center, Ural Branch of the Russian Academy of Sciences, Syktyvkar, Russian Federation

Abstract: Asymmetric aldol reactions of isatin and 4,6-dibromoisatin with acetone are efficiently catalyzed by β-amino alcohols derived from α-pinene and 3-carene. The target compounds can be isolated by crystallization from toluene, which eliminates the need for using chromatography and makes the asymmetric synthesis of (R)-convolutamydine A (up to 94% ee and yield 75%) simple and convenient.

Keywords: aldol reaction, β-amino alcohols, 3-carene, α-pinene, isatin, 4,6-dibromoisatin, convolutamydine A.

Language: English

DOI: 10.1016/j.mencom.2020.03.005

Bibliographic databases:

•