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

Literature Information

Publication Date 2005-07-27
DOI 10.1039/B506601H
Impact Factor 6.222
Authors

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


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Abstract

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

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