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2005
Pyridine derivatives
R 0380
A Chiral Base Desymmetrization—Ring-Closing Metathesis Route to Chiral AzaSynthesis of Core Structures Related to Pinnaic Acid and Halichlo16- 130 spirocycles:
rine. — The synthesis of a range of enantioenriched azaspirocyclic compounds, namely analogues of pinnaic acid, is presented. First step is the desymmetrization of piperidine diester (I) in 90% e.e. with a chiral base and allyl bromide. Further transformations
then provide ene ester (VI) or aldehyde (X), in which a second terminal double bond is
installed either by Claisen rearrangement or by Grignard addition, resp., followed by
ring closing metathesis. — (HUXFORD, T.; SIMPKINS*, N. S.; Synlett 2004, 13,
2295-2298; Sch. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK; Eng.) —
Mischke
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