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 -