Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticle

DOI

Author(s)

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

School/Research organisations

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.
Close

Details

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

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Understanding a hydroformylation catalyst that produces branched aldehydes from alkyl alkenes

    Dingwall, P., Fuentes, J. A., Crawford, L., Slawin, A. M. Z., Buehl, M. & Clarke, M. L. 25 Oct 2017 In : Journal of the American Chemical Society. In press

    Research output: Contribution to journalArticle

  2. A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

    Harkness, G. J. & Clarke, M. L. 1 Sep 2017 In : European Journal of Organic Chemistry. 2017, 32, p. 4859-4863 5 p.

    Research output: Contribution to journalArticle

  3. Composition of catalyst resting states of hydroformylation catalysts derived from bulky mono-phosphorus ligands, rhodium dicarbonyl acetylacetonate and syngas

    How, R. C., Dingwall, P., Hembre, R. T., Ponasik, J. A., Tolleson, G. S. & Clarke, M. L. Jun 2017 In : Molecular Catalysis. 434, p. 116-122 7 p.

    Research output: Contribution to journalArticle

  4. A highly active manganese catalyst for enantioselective ketone and ester hydrogenation

    Widegren, M. B., Harkness, G. J., Slawin, A. M. Z., Cordes, D. B. & Clarke, M. L. 15 May 2017 In : Angewandte Chemie. 129, 21, p. 5919-5922 4 p.

    Research output: Contribution to journalArticle

  5. A Highly Active Manganese Catalyst for Enantioselective Ketone and Ester Hydrogenation

    Widegren, M. B., Harkness, G. J., Slawin, A. M. Z., Cordes, D. B. & Clarke, M. L. 15 May 2017 In : Angewandte Chemie International Edition. 56, 21, p. 5825-5828 4 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement

    Kasten, K., Slawin, A. M. Z. & Smith, A. D. 6 Oct 2017 In : Organic Letters. 19, 19, p. 5182-5185 4 p.

    Research output: Contribution to journalArticle

  2. Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

    Fugard, A. J., Thompson, B. K., Slawin, A. M. Z., Taylor, J. E. & Smith, A. D. 4 Dec 2015 In : Organic Letters. 17, 23, p. 5824-5827 4 p.

    Research output: Contribution to journalArticle

  3. Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers

    Healy, A. R., Vinale, F., Lorito, M. & Westwood, N. J. 6 Feb 2015 In : Organic Letters. 17, 3, p. 692-695 4 p.

    Research output: Contribution to journalArticle

  4. Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates

    Stark, D. G., O’Riordan, T. J. C. & Smith, A. D. 8 Dec 2014 In : Organic Letters. In press

    Research output: Contribution to journalArticle

ID: 249994299