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Molecules 2012, 17(12), 13864-13878; doi:10.3390/molecules171213864
Article

Efficient Preparation of α-Ketoacetals

, , ,  and *
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas del IPN, Prol. de Carpio y Plan de Ayala S/N, Col. Santo Tomás, Deleg. Gustavo A. Madero, México, DF 11340, Mexico
* Author to whom correspondence should be addressed.
Received: 22 October 2012 / Revised: 31 October 2012 / Accepted: 19 November 2012 / Published: 22 November 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

The Weinreb amides 2a,b were prepared from the α,α-dimethoxyacetic acids 1c,d. A number of representative nucleophilic additions (RMgX and RLi) on 2 afforded α-ketoacetals 3aj in 70–99% yield. These compounds represent a versatile arrangement of functional groups of significant synthetic value, as demonstrated in the synthesis of (±)-salbutamol.
Keywords: α,α-dimethoxyacids; Weinreb amide; Grignard reagents; α-ketoacetals; salbutamol α,α-dimethoxyacids; Weinreb amide; Grignard reagents; α-ketoacetals; salbutamol
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Ayala-Mata, F.; Barrera-Mendoza, C.; Jiménez-Vázquez, H.A.; Vargas-Díaz, E.; Zepeda, L.G. Efficient Preparation of α-Ketoacetals. Molecules 2012, 17, 13864-13878.

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