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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 (CC BY 3.0).

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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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