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Communication

Chem. Commun., 2005, 4285 - 4287, DOI: 10.1039/b506601h


Mechanistic subtleties in the cyclopentannelation of allenolate allyl carbamates: the origin of the center-to-center chirality transfer

Olalla Nieto Faza, Carlos Silva López, Rosana Álvarez and Ángel R. de Lera


The stereospecific rearrangement of allene carbamates i to alkylidenecyclopentenones iii is concerted, displays charge donation from the *allenonate to the *C-leaving group, and shows mechanistic features of both pericyclic and ionic processes, modulated in part by the degree of ionic interaction (OLi+) in the putative intermediate allenolate ii.

Graphical abstract image for this article  (ID: b506601h)