Organic Letters
Organic Letters
5 years ago

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
Shahnawaz Khan, Qazi Naveed Ahmed, Atul Kumar
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02016

DOI: 10.1021/acs.orglett.7b02016

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