Anderson, JC;
Campbell, IB;
Campos, S;
Rundell, CD;
Shannon, J;
Tizzard, GJ;
(2017)
Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles.
Organic Letters
, 19
(7)
pp. 1918-1921.
10.1021/acs.orglett.7b00679.
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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.
| Type: | Article |
|---|---|
| Title: | Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/acs.orglett.7b00679 |
| Publisher version: | http://dx.doi.org/10.1021/acs.orglett.7b00679 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1546121 |
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