ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 30. Facile Synthesis, by the Matteson Asymmetric Homologation Procedure, of α-Methyl Boronic Acids not Available from Asymmetric Hydroboration and Their Conversion into the Corresponding Aldehydes, Ketones, Carboxylic Acids, and Amines of High Enantiomeric Purity.
Abstract
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ChemInform Abstract
The Matteson asymmetric homologation procedure of the optically pure pinanediol boronate (I) with lithiodichloromethane generated in situ gives the chloromethylboranate derivative (III). It is treated with Grignard reagents such as (IV) forming chiral homologous boranates such as (V). This is converted to the aldehyde (VII), the ketone (XII), or the amine (XIII) as shown in the reaction scheme. Numerous further examples are given in the original paper.
