Author(s)
T. K. Hutton, K. Muir, D. J. Procter
ISBN
1523-7060
Publication year
2002
Periodical
Organic Letters
Periodical Number
14
Volume
4
Pages
2345-2347
Author Address
[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.