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Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using ( S )-(+)-2,4,6-Trimethylphenylsulfinamide

2003; American Chemical Society; Volume: 68; Issue: 18 Linguagem: Inglês

10.1021/jo030142m

1520-6904

Franklin A. Davis, Tokala Ramachandar, Yongzhong Wu,

Sulfur-Based Synthesis Techniques

The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.