Stereoselective Synthesis of Branched Aldol Products

The aldol reaction occupies a prominent position in organic synthesis and remains one of the most used methodologies for producing chiral compounds in non-racemic form. Metal dienolates are versatile carbanions that can react with carbonyl electrophiles to afford linear or branched products. The stereo- and regioselectivities of the aldol reaction have been extensively examined for various metal salts including Zn(II), Si(IV), Sn(IV), Li(I), B(III) or In(III) because their linear and branched aldol products are useful building blocks for accessing natural products. Recently, the laboratory of Professor Rai-Shung Liu at the National Tsing-Hua University (Taiwan) developed a Zn(II)-catalyzed hydrative aldol reaction to generate stable O-bound Zn(II)-dienolates that can react with aldehydes to afford branched aldol products stereoselectively.

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