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Catalytic Enantioselective Conjugate Addition of Nitromethane to α′-Hydroxy Enones as Surrogates of α,β-Unsaturated Carboxylic Acids and Aldehydes

✍ Scribed by Claudio Palomo; Raquel Pazos; Mikel Oiarbide; Jesús M. García

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
85 KB
Volume
348
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

No base is required for the Mg(II)‐catalyzed conjugate addition of nitromethane to α′‐hydroxy enones in the presence of molecular sieves. Good enantioselectivities are attained using 3 or 4 Å MS and about 10 mol % of Mg(OTf)~2~‐chiral bisoxazoline complexes. Elaboration of the adducts through oxidative cleavage of the ketol moiety provides an entry to enantioenriched γ‐nitro carboxylic acids, while a sequential carbonyl reduction‐diol oxidation yields the corresponding aldehydes.

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