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Synthesis

Ladder polyethers

May 8, 2006 | A version of this story appeared in Volume 84, Issue 19

Timothy F. Jamison and colleagues' research, showing that trimethylsilyl groups can be used in a one-step epoxide-opening cascade reaction to prepare ladder polyethers, is significant and exciting (C&EN, Jan. 16, page 8). Your readers may be interested in some of the background on the individual steps.

The use of trimethylsilyl groups to direct epoxide opening by oxygen nucleophiles was first demonstrated by G. H. Whitham (1976) and me (1977). The desilylation of simple b-hydroxysilanes (homo-Brook rearrangements), and that these reactions take place with retention of stereochemistry, was demonstrated in work that I did with Anne M. Hudrlik and Peter E. Kulkarni in 1982. The combination of these two steps to give a defined isomer of the ring-opened product, where the analogous reaction of the epoxide having H in place of the silicon group gave mixtures, was reported in 1988 (Tetrahedron Lett. 1988, 29, 6395).

Paul F. Hudrlik
Washington, D.C.

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