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Issue 2, 2013
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α-Haloaldehydes: versatile building blocks for natural product synthesis

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Abstract

Covering: up to July 2012

The diastereoselective addition of organometallic reagents to α-chloroaldehydes was first reported in 1959 and occupies a historically significant role as the prototypical reaction for Cornforth's model of stereoinduction. Despite clear synthetic potential for these reagents, difficulties associated with producing enantiomerically enriched α-haloaldehydes limited their use in natural product synthesis through the latter half of the 20th century. In recent years, however, a variety of robust, organocatalytic processes have been reported that now provide direct access to optically enriched α-haloaldehydes and have motivated renewed interest in their use as building blocks for natural product synthesis. This Highlight summarizes the methods available for the enantioselective preparation of α-haloaldehydes and their stereoselective conversion into natural products.

Graphical abstract: α-Haloaldehydes: versatile building blocks for natural product synthesis

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Article information


Submitted
01 Nov 2012
First published
20 Dec 2012

Nat. Prod. Rep., 2013,30, 227-236
Article type
Highlight

α-Haloaldehydes: versatile building blocks for natural product synthesis

R. Britton and B. Kang, Nat. Prod. Rep., 2013, 30, 227
DOI: 10.1039/C2NP20108A

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