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Samarium(II)-mediated reactions of gamma,delta-unsaturated ketones. Cyclization and fragmentation processes

Author(s): T. K. Hutton, K. Muir, D. J. Procter

Abstract:
[GRAPHICS] On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

Full version: Available here

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ISBN: 1523-7060
Publication Year: 2002
Periodical: Organic Letters
Periodical Number: 14
Volume: 4
Pages: 2345-2347
Author Address: