Section 10
Chapter 9,632

The tetrahydrooxazinone way to enantiopure alpha-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

Agami, C.; Bihan, D.; Hamon, L.; Puchot Kadouri, C.

Tetrahedron 54(35): 10309-10316


ISSN/ISBN: 0040-4020
Accession: 009631286

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Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enantiopure either cis or trans 3-vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AM1 calculations.

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