Base-Controlled Reactions through an Aldol Intermediate Formed between 2‑Oxoaldehydes and Malonate Half Esters

Base-Controlled Reactions through an Aldol Intermediate Formed between 2‑Oxoaldehydes and Malonate Half Esters

A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) c...

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Veröffentlicht in:Organic letters 2017-09, Vol.19 (18), p.4730-4733
Hauptverfasser: Kumar, Atul, Khan, Shahnawaz, Ahmed, Qazi Naveed
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creator Kumar, Atul
Khan, Shahnawaz
Ahmed, Qazi Naveed
description A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.
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title Base-Controlled Reactions through an Aldol Intermediate Formed between 2‑Oxoaldehydes and Malonate Half Esters
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