ChemInform Abstract: A Convenient Method for Synthesis of Optically Active β- Hydroxyamines from Primary Amines Through Enecarbamates as Key Intermediates.

✍ Scribed by Y. MATSUMURA; T. OHISHI; C. SONODA; T. MAKI; M. WATANABE

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199732074

✦ Synopsis

A Convenient Method for Synthesis of Optically Active β-Hydroxyamines from Primary Amines Through Enecarbamates as Key Intermediates.

-The new method for the synthesis of title compounds (IV) consists of three steps: an earlier reported electrochemical α-methoxylation of N-protected primary amines leading to carbamates (I), an improved procedure for methanol elimination yielding enecarbamates (II)/(III), and the asymmetric hydroboration of trans-compounds (II) with (+)-isopinocampheylborane obtaining the target compounds with moderate e.e. , except (IVa). The usefulness of the method is demonstrated by the transformation of (IVd) to the alkaloid (V). -(MATSUMURA, Y.;