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ChemInform Abstract: A Radical Approach to Asymmetric Aldol Synthesis.

โœ Scribed by P. GARNER; R. LESLIE; J. T. ANDERSON

Publisher
John Wiley and Sons
Year
2010
Weight
30 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

1997 stereochemistry stereochemistry (general, optical resolution) O 0030

05 -061

A Radical Approach to Asymmetric Aldol Synthesis.

-A conceptually novel approach to asym. aldol synthesis is reported, which is based on the stereocontrolled addition of a chiral hydroxyalkyl radical equivalent to a nitroalkene. The reaction sequence starts with glycosides (I) via intermediates (IV) and (V). Glycoside cleavage with concomitant production of the free aldol is potentially difficult because of the ease with which the aldol production can suffer dehydration. However the method shown releases the free aldols (VII) without dehydration and the sugar-derived chiral auxiliary for reuse. -

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