α-Haloaldehydes: versatile building blocks for natural product synthesis.

Abstract:

: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.

journal_name

Nat Prod Rep

journal_title

Natural product reports

authors

Britton R,Kang B

doi

10.1039/c2np20108a

subject

Has Abstract

pub_date

2013-02-01 00:00:00

pages

227-36

issue

2

eissn

0265-0568

issn

1460-4752

journal_volume

30

pub_type

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