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Synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: a silicon mediated total synthesis of (+)-carpamic acid

✍ Scribed by Rekha Singh; Sunil K Ghosh

Book ID: 104252104
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 259 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01853-1

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✦ Synopsis

A stereoselective total synthesis of (+)-carpamic acid 1 has been achieved from the s-symmetric 3-[dimethyl(phenyl)silyl]glutaric anhydride 11 featuring its asymmetric desymmetrisation using oxazolidinone 12. The dimethyl(phenyl)silyl group is not only acting as a masked hydroxy group but also stereodirects ester enolate methylation and facilitates the Curtius reaction of the b-silyl-amide 23. A highly stereoselective hydrogenation of the imine 10 is the key step in the construction of the all cis-2,3,6-trisubstituted piperidine.

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