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Synthesis of Substituted-( l )-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol

2001; American Chemical Society; Volume: 3; Issue: 26 Linguagem: Inglês

10.1021/ol016861+

1523-7060

Do Kyu Pyun, Cheol Hae Lee, Hyun‐Joon Ha, Chan Sun Park, Jae‐Won Chang, Won Koo Lee,

Asymmetric Synthesis and Catalysis

Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield. [reaction: see text]