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Ring Expansion Induced by DAST: Synthesis of Substituted 3‐Fluoropiperidines from Prolinols and 3‐Fluoroazepanes from 2‐Hydroxymethylpiperidines
Author(s) -
Déchamps Ingrid,
Gomez Pardo Domingo,
Cossy Janine
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700237
Subject(s) - chemistry , optically active , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry
Optically active prolinols can be converted into optically active 3‐fluoropiperidines by treatment with DAST. The reaction often produces 2‐fluoromethylpyrrolidines as byproducts. The ring expansion was also applied to 2‐hydroxypiperidines to produce 3‐fluoroazepanes. The rearrangement proceeds via an aziridinium intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)