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

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.

Citation

Pittaway , R , Fuentes , J A & Clarke , M L 2017 , ' Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation : synthesis of functionalized piperidines and amino-alcohols ' , Organic Letters , vol. 19 , no. 11 , pp. 2845-2848 . https://doi.org/10.1021/acs.orglett.7b01049

Publication

Organic Letters

Status

Peer reviewed

DOI

https://doi.org/10.1021/acs.orglett.7b01049

ISSN

1523-7060

Type

Journal article

Rights

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

Description

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

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/13388