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Base controlled diastereoselective synthesis of either anti- or syn-β-aminonitriles

Base controlled diastereoselective synthesis of either anti- or syn-β-aminonitriles
Base controlled diastereoselective synthesis of either anti- or syn-β-aminonitriles
Deprotonation of secondary alkane nitriles with nBuLi and addition to aryl imines gives kinetic anti-β-aminonitriles. Use of LHMDS allows reversible protonation of the reaction intermediate to give syn-β-aminonitriles. The pure diastereosiomers can be isolated in good yields, and the mechanism was elucidated.
1523-7060
1918-1921
Anderson, James C.
af851b46-35f3-48c1-b490-1f411364b7fe
Campbell, Ian B.
6b184e7b-5ec8-43c5-8b44-97b163883fa1
Campos, Sebastien
56181049-28c5-44aa-91c3-2e8d68d0c0b4
Rundell, Christopher
d14d146c-ee7a-455a-b99a-8b42fb8b671a
Shannon, Jonathan
6ea3174d-64ae-4b64-8a20-41ce953b7fb9
Tizzard, Graham
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Anderson, James C.
af851b46-35f3-48c1-b490-1f411364b7fe
Campbell, Ian B.
6b184e7b-5ec8-43c5-8b44-97b163883fa1
Campos, Sebastien
56181049-28c5-44aa-91c3-2e8d68d0c0b4
Rundell, Christopher
d14d146c-ee7a-455a-b99a-8b42fb8b671a
Shannon, Jonathan
6ea3174d-64ae-4b64-8a20-41ce953b7fb9
Tizzard, Graham
8474c0fa-40df-43a6-a662-7f3c4722dbf2

Anderson, James C., Campbell, Ian B., Campos, Sebastien, Rundell, Christopher, Shannon, Jonathan and Tizzard, Graham (2017) Base controlled diastereoselective synthesis of either anti- or syn-β-aminonitriles. Organic Letters, 19 (7), 1918-1921. (doi:10.1021/acs.orglett.7b00679).

Record type: Article

Abstract

Deprotonation of secondary alkane nitriles with nBuLi and addition to aryl imines gives kinetic anti-β-aminonitriles. Use of LHMDS allows reversible protonation of the reaction intermediate to give syn-β-aminonitriles. The pure diastereosiomers can be isolated in good yields, and the mechanism was elucidated.

Text
Revised Org. Lett. 160317 - Accepted Manuscript
Available under License University of Southampton Accepted Manuscript Licence.
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Accepted/In Press date: 17 March 2017
e-pub ahead of print date: 21 March 2017
Published date: 7 April 2017
Organisations: Chemistry Research Support

Identifiers

Local EPrints ID: 410904
URI: http://eprints.soton.ac.uk/id/eprint/410904
DOI: doi:10.1021/acs.orglett.7b00679
ISSN: 1523-7060
PURE UUID: c7b55c3c-17c9-4fb6-9e86-ed2cc9da53a1
ORCID for Graham Tizzard: ORCID iD orcid.org/0000-0002-1577-5779

Catalogue record

Date deposited: 09 Jun 2017 16:31
Last modified: 16 Mar 2024 05:24

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Contributors

Author: James C. Anderson
Author: Ian B. Campbell
Author: Sebastien Campos
Author: Christopher Rundell
Author: Jonathan Shannon
Author: Graham Tizzard ORCID iD

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