Monday, October 28, 2013

Organoytterbium Ate Complexes Extend the Value of Cyclobutenediones as Isoprene Equivalents

by Emma Packard, David D. Pascoe, Jacques Maddaluno, Théo P. Gonçalves, David C. Harrowven*


Thumbnail image of graphical abstract

Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (−)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.

Angewandte Chemie Internation Edition
Article first published online: 23 OCT 2013

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