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

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

doi:10.1021/acs.orglett.7b01049

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

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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2845-2848
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	11
Early online date	17 May 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b01049
Publication status	Published - 2 Jun 2017

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allylglycinehffinalv2pdfvers
Copyright © 2017 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acs.orglett.7b01049
Accepted author manuscript, 491 KB

Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations
Clarke, M. (PI) & Buehl, M. (CoI)
EPSRC
1/09/14 → 30/11/17
Project: Standard

Data underpinning - Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation: synthesis of functionalised piperidines and amino-alcohols
Pittaway, R. (Creator), Fuentes, J. A. (Contributor) & Clarke, M. L. (Supervisor), University of St Andrews, 11 Oct 2017
DOI: 10.17630/24f40cf5-ead3-4220-a297-881c40009402
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title = "Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation: synthesis of functionalized piperidines and amino-alcohols",

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.",

author = "Rachael Pittaway and Fuentes, {Jos{\'e} A.} and Clarke, {Matthew L.}",

note = "Financial support by EPSRC DTG grant and EP/M0038868/1 is gratefully acknowledged.",

year = "2017",

month = jun,

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doi = "10.1021/acs.orglett.7b01049",

language = "English",

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pages = "2845--2848",

journal = "Organic Letters",

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T1 - Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation

T2 - synthesis of functionalized piperidines and amino-alcohols

AU - Pittaway, Rachael

AU - Fuentes, José A.

AU - Clarke, Matthew L.

N1 - Financial support by EPSRC DTG grant and EP/M0038868/1 is gratefully acknowledged.

PY - 2017/6/2

Y1 - 2017/6/2

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.7b01049

DO - 10.1021/acs.orglett.7b01049

M3 - Article

SN - 1523-7060

VL - 19

SP - 2845

EP - 2848

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

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

Abstract

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Projects

Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations

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

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