Beilstein J. Org. Chem.2008,4, No. 17, doi:10.3762/bjoc.4.17
-addition to α,β-unsaturated esters, ketones, sulfone, nitriles and propynoates.
Supporting Information
Supporting Information File 83: Experimental procedures, full spectroscopic data and spectra.
Supporting Information File 84: Spectra.
Acknowledgements
Support of our work by the Loker Hydrocarbon
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Graphical Abstract
Scheme 1:
Reaction mechanism for phosphine catalyzed 1,4-addition to α,β-unsaturated compounds.
Beilstein J. Org. Chem.2007,3, No. 39, doi:10.1186/1860-5397-3-39
University, Private Bag 11 222, Palmerston North, New Zealand 10.1186/1860-5397-3-39 Abstract We have developed a general strategy for the synthesis of 2,5-syn disubstituted pyrrolidines that is based on the multi-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation. This methodology was
, such as tetrahydrofurans and pyrrolidines, makes these motifs attractive targets for synthesis. Over the last decade we have developed a powerful general strategy for the preparation of such compounds based upon the multi-faceted reactivity of the sulfone group and the formally disfavoured 5-endo-trig
mode of cyclisation. [1][2][3][4][5][6] The methodology allows the conversion of epoxides (X = O) or aziridines (X = N-PG) (2) into the desired trisubstituted tetrahydrofurans or pyrrolidines (5) via a series of sulfone-mediated transformations (Scheme 1). Ring-opening 2 with the sulfone-stabilised
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Graphical Abstract
Scheme 1:
General strategy for the synthesis of heterocycles via 5-endo-trig cyclisation