Synthesis of 3-aminochroman derivatives by radical cyclization

G Pavé, S Usse-Versluys, MC Viaud-Massuard…

Index: Pave, Gregoire; Usse-Versluys, Stephanie; Viaud-Massuard, Marie-Claude; Guillaumet, Gerald Organic Letters, 2003 , vol. 5, # 23 p. 4253 - 4256

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Citation Number: 28

Abstract

Enantiomerically pure 5-acetyl-3-amino-3, 4-dihydro-2 H-1-benzopyran and methyl 3-amino- 3, 4-dihydro-2 H-1-benzopyran-5-carboxylate were successfully synthesized starting from d- or l-serine. The formation of the benzopyran ring involved a radical cyclization step. The enantiomeric purities of the final aminochroman derivatives were determined by capillary electrophoresis using β-cyclodextrins as a chiral selector.