ChemInform Abstract: Lewis Acid Induced N-Methyleneamine Equivalents. Part 4. Addition of 2- Trimethylsilyloxyfuran to Catalytically Generated N-Methyleneamine Equivalents: Synthesis of 5-Aminomethyl-2,5-dihydrofuran-2-ones.

✍ Scribed by H.-J. HA; K.-H. KANG; Y.-G. AHN; S.-J. OH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199734115

✦ Synopsis

Lewis Acid Induced N-Methyleneamine Equivalents. Part 4. Addition of 2-Trimethylsilyloxyfuran to Catalytically Generated N-Methyleneamine Equivalents: Synthesis of 5-Aminomethyl-2,5dihydrofuran-2-ones.

-Treatment of 1,3,5-hexahydrotriazines (I) or N-methoxymethylanilines ( IV) with catalytic Lewis acids (see optimized conditions in the scheme) generates N-methyleneamine equivalents which readily react with 2-trimethylsilyloxyfuran (II) to the 5-aminomethyl-2,5-dihydrofuran-2ones (III). The chiral version of the reaction starting from the enantiopure triazine (V) proceeds with only moderate diastereoselectivity. -(HA, H.-J.;