Noscapine-derived β-amino alcohols as new organocatalysts for enantioselective addition of diethylzinc to aldehydes.

Mohebbi, Maryam; Salehi, Peyman; Bararjanian, Morteza; Ebrahimi, Samad

In this paper, synthesis of two derivatives of noscapine and their application as organocatalysts in the asymmetric addition of diethylzinc to aromatic aldehydes is reported. The first catalyst ( 2) was synthesized by the reduction of lactone ring of noscapine to form the corresponding diol, and the second one ( 3) was prepared by tert-butyl dimethyl silylation of the primary hydroxyl group of 2. Excellent yields and high ees up to 95% were obtained by using 3 as the catalyst. To the best of our knowledge, this is the first report on the application of lactone ring opened noscapinoid compounds as organocatalysts in asymmetric reactions.

NOSCAPINE; CHEMICAL derivatives; HYDROXYL group; AMINO alcohol synthesis; LACTONES

Journal of the Iranian Chemical Society, 2018, Vol 15, Issue 1, p47

1735-207X

Academic Journal

10.1007/s13738-017-1207-9