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Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation: synthesis of functionalized piperidines and amino-alcohols

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Author(s)

Rachael Pittaway, José A. Fuentes, Matthew L. Clarke

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Abstract

Starting from readily available allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin.
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Original languageEnglish
Pages (from-to)2845-2848
Number of pages4
JournalOrganic Letters
Volume19
Issue number11
Early online date17 May 2017
DOIs
StatePublished - 2 Jun 2017

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