Selective Synthesis of cis‐2‐Vinyl‐3‐alkylaziridines and 3‐Pyrrolines from Common Intermediates (Z)‐4‐N‐Arylsulfonylaminoalk‐2‐en‐1‐ols.

1999 
A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl)amino-4-alkylbut-2-en-1-ols, is described. Palladium(0)-catalyzed reactions of methyl carbonates of the N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols give exclusively the corresponding 3-pyrrolines in high yields. A synthesis of biologically important (S)-3,4-dehydroproline is also presented.
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