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Title

Synthesis of (-)-Pinidine via asymmetric, electrophilic enolate hydroxyamination/nitrone reduction

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Oppolzer, Wolfgang
Published in Helvetica Chimica Acta. 1993, vol. 76, no. 2, p. 957-962
Abstract Enantiomerically pure(−)-pinidine (1) has been synthesized in 18.5% overall yield by a nine-step sequence starting from keto-ester 2. The key step 5 [RIGHTWARDS ARROW] 6 involves an asymmetric, electrophilic enolate hydroxyamination. Diastereoselective hydrogenation of nirtone 6 ensures the cis-relation between the substituents at C(2) and C(6) in piperidine 7.
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Other version: http://doi.wiley.com/10.1002/hlca.19930760218
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OPPOLZER, Wolfgang, MERIFIELD, Eric. Synthesis of (-)-Pinidine via asymmetric, electrophilic enolate hydroxyamination/nitrone reduction. In: Helvetica Chimica Acta, 1993, vol. 76, n° 2, p. 957-962. https://archive-ouverte.unige.ch/unige:85067

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