Abstract
A convenient and environmentally attractive one-pot two-step process for the synthesis of β-adrenergic blockers via Shi's organocatalytic epoxidation of terminal alkenes and subsequent aminolysis reaction of epoxides with isopropylamine under mild reaction conditions has been developed.
Highlights
The synthesis of enantiomerically pure chiral drugs and bioactive compounds still remains a challenging task for organic chemists.Asymmetric syntheses employing chiral catalysts is among the most common routes to optically pure compounds
As far as we are aware, this method has never been applied to the synthesis of b-adrenergic blockers
We envisaged that employing versatile Shi epoxidation reaction as a key step to build up selected b-adrenergic blockers 1–3 in a onepot process would be of synthetic value
Summary
The synthesis of enantiomerically pure chiral drugs and bioactive compounds still remains a challenging task for organic chemists.Asymmetric syntheses employing chiral catalysts is among the most common routes to optically pure compounds. In 2011, we introduced a one-pot multi-step synthetic approach towards 1,2-amino alcohols employing oxazaborolidine organocatalysts, prepared in situ from a-amino acids.[8] This new strategy we applied for the highly enantioselective synthesis of selected b-adrenergic blockers 1–3 (Fig. 1) via onepot sequential transformations: reduction of a-halo ketones/ epoxide formation/aminolysis reaction.[8] Pharmaceuticals pronethalol (1),[9] nifenalol (2)[10] and dichloroisoproterenol (3)[11] are of great importance in the therapy of asthma, bronchitis and congestive heart failure.[12]
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