Final published version
Research output: Contribution to Journal/Magazine › Journal article
Research output: Contribution to Journal/Magazine › Journal article
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TY - JOUR
T1 - Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N-Aryl Pyrrolidines
AU - Moss, Sam G.
AU - Pocock, Ian A.
AU - Sweeney, Joseph B.
N1 - Author was employed at another UK HEI at the time of submission and was deposited at Huddersfield University Repository, see link http://eprints.hud.ac.uk/id/eprint/31857/
PY - 2017/1/1
Y1 - 2017/1/1
N2 - We report a new method for the synthesis of novel N-aryl proline analogues. By reacting an aryne precursor with N-(2-malonyl) tetrahydropyridines in the presence of tetrabutylammonium fluoride (TBAF), a tandem aryne-capture/anion isomerisation/[2,3]-sigmatropic rearrangement is induced, leading to good yields of 3-substituted N-aryl-2-acylpyrrolidines. These products are known subunits of biological probes, sensors and drug-like fragments, and are not easily accessed directly by other methods. The reaction is also notable as the first [2,3]-rearrangement of cyclic ammonium ylides at room temperature.
AB - We report a new method for the synthesis of novel N-aryl proline analogues. By reacting an aryne precursor with N-(2-malonyl) tetrahydropyridines in the presence of tetrabutylammonium fluoride (TBAF), a tandem aryne-capture/anion isomerisation/[2,3]-sigmatropic rearrangement is induced, leading to good yields of 3-substituted N-aryl-2-acylpyrrolidines. These products are known subunits of biological probes, sensors and drug-like fragments, and are not easily accessed directly by other methods. The reaction is also notable as the first [2,3]-rearrangement of cyclic ammonium ylides at room temperature.
KW - metal-free
KW - N-aryl pyrrolidine
KW - sigmatropic rearrangement
KW - tandem
KW - ylides
U2 - 10.1002/chem.201605290
DO - 10.1002/chem.201605290
M3 - Journal article
AN - SCOPUS:85006246870
VL - 23
SP - 101
EP - 104
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 1
ER -